Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you

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Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
2020 – 2021
Tax Planning Guide
Year-round strategies to make the tax laws work for you

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Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
Tax planning in
unprecedented times

       t has become a cliché in 2020, but what word other than “unprecedented” can be used to
    I  describe the events we’ve experienced this year? During such times, tax planning is far from
       top of mind. But it’s still important. Smart tax planning can soften the impact of an uncertain
economy and provide much-needed relief to owners of struggling businesses.

To take advantage of all available breaks, you need to be aware of some major changes under this year’s
Coronavirus Aid, Relief and Economic Security (CARES) Act and last year’s Setting Every Community
Up for Retirement Enhancement (SECURE) Act. You also can’t forget about the massive Tax Cuts and
Jobs Act (TCJA) that generally went into effect two years ago but still impacts tax planning. Plus, it’s
possible that there could be more tax law changes before year end — or that the potential for changes
next year could affect 2020 planning.

This guide provides an overview of some of the most significant tax law changes going into effect this
year and other key tax provisions you need to be aware of. It offers a variety of strategies for minimizing
your taxes in the current tax environment. Use it to work closely with your tax advisor to identify the
best strategies for your particular situation. He or she also can keep you apprised of any new tax law
developments that might affect you.

Contents
Income & Deductions................................................2             Click here

Executive Compensation...........................................6               Click here

Investing....................................................................8   Click here

Real Estate...............................................................12     Click here

Business Ownership.................................................14            Click here

Charitable Giving....................................................16          Click here

Family & Education.................................................18            Click here

Retirement...............................................................20      Click here

Estate Planning........................................................22        Click here

Tax Rates..................................................................24    Click here
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
2 Income & Deductions

Control the timing of income and
deductions to your tax advantage

                          ax rates on “ordinary income”      y	U.S. Treasury bill income, and                     Suspension of miscellaneous itemized
                  T       are higher than those that
                          apply to much of your
                                                             y	Retirement plan distributions, to
                                                                                                                   deductions subject to the 2% floor.
                                                                                                                   This deduction for expenses such as
                                                                the extent they won’t be subject
                investment income. Ordinary income                                                                 certain professional fees, investment
                                                                to early-withdrawal penalties and
                generally includes salary, income from                                                             expenses and unreimbursed employee
                                                                aren’t required. (See page 20.)
                self-employment or business activities,                                                            business expenses is suspended through
                interest, and distributions from tax-                                                              2025. While this eliminates the home
                deferred retirement accounts. Some of        Some expenses with potentially
                                                                                                                   office deduction for employees who
                it may also be subject to payroll tax,       controllable timing are mortgage
                                                                                                                   work from home (even if your employer
                or you may have to pay the alternative       interest, investment interest expense
                                                                                                                   has required it during the pandemic),
                minimum tax (AMT), under which               and charitable contributions.
                                                                                                                   if you’re self-employed, you may still be
                different tax rates apply. This is why                                                             able to deduct home office expenses.
                careful planning for ordinary income         Impact of the TCJA                                    (See page 12.)
                and deductible expenses continues to         on timing strategies
                be important.                                The TCJA has made timing income                       More-restricted personal casualty and
                                                             and deductions more challenging                       theft loss deduction. Through 2025, this
                Timing income and expenses                   because some strategies that tax-                     itemized deduction is suspended except
                Smart timing of income and expenses          payers used to implement no longer                    if the loss was due to an event officially
                can reduce your tax liability, and poor      are making sense. Here’s a look and                   declared a disaster by the President.
                timing can unnecessarily increase it.        some significant changes that have
                When you don’t expect to be subject          affected deductions:                                  Increased standard deduction. The
                to the AMT (see page 3) in the current                                                             TCJA nearly doubled the standard
                year or the next year, deferring income to   Reduced deduction for state and                       deduction. While many higher-income
                the next year and accelerating deductible    local tax. Property tax used to be a                  taxpayers will still benefit from itemiz-
                expenses into the current year may be        popular expense to time. But with the                 ing, some — such as those in low-tax
                a good idea. Why? Because it will defer      TCJA’s limit on the state and local                   states, who don’t have mortgages or
                tax, which usually is beneficial.            tax deduction, property tax timing                    who aren’t charitably inclined — may
                                                             will likely provide little, if any, benefit           now save more tax by claiming the
                But when you expect to be in a higher        for higher-income taxpayers. (See                     standard deduction. (See Chart 1 for
                tax bracket next year — or you expect        Case Study 1 at right.) If you reside                 the 2020 standard deduction amounts.)
                tax rates to rise — the opposite approach    in a state with no, or low, income tax,
                may be beneficial: Accelerating income       this change might be less relevant.                   Tax-advantaged
                will allow more income to be taxed at        But keep in mind that deducting sales                 saving for health care
                your current year’s lower rate. And defer-   tax instead of income tax may be
                                                                                                                   If medical expenses not paid via
                ring expenses will make the deductions       beneficial, especially if you purchased
                                                                                                                   tax-advantaged accounts or reimburs-
                more valuable, because deductions save       a major item, such as a car or boat.
                                                                                                                   able by insurance exceed a certain
                more tax when you’re subject to a higher
                tax rate.                                     CHART 1
                                                                              2020 standard deduction
                Whatever the reason behind your
                desire to time income and expenses,                           Filing status                               Standard deduction1
                you may be able to control the timing          Singles and separate filers                                        $12,400
                of these income items:
                                                               Heads of households                                                $18,650

                y	Bonuses,                                    Joint filers                                                       $24,800
                                                               1
                                                                	Taxpayers age 65 or older or blind can claim an additional standard deduction: $1,300 if married,
                y	Consulting or other self-employment           $1,650 if unmarried.
                   income,
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
Income & Deductions 3

                                                                                       FSA. You can redirect pretax income
 CASE        Factor state and local tax                                                to an employer-sponsored Flexible
 STUDY 1     deduction limits into timing strategies                                   Spending Account up to an employer-
                                                                                       determined limit — not to exceed $2,750
  Last year, Justin earned a promotion along with a significant salary increase and
                                                                                       in 2020. The plan pays or reimburses you
  bonus, and his state income tax liability increased accordingly. When he filed
  his 2019 tax return, he was surprised to find that he could no longer deduct all
                                                                                       for qualified medical expenses. What
  of his state and local income and property taxes. This meant that prepaying his      you don’t use by the plan year’s end, you
  2019 property tax bill due in early 2020 hadn’t helped him. He’d always done his     generally lose — though your plan might
  income taxes himself, but he decided it was time to consult a tax professional.      allow you to roll over up to $550 to 2021.
                                                                                       Or it might give you a 2½-month grace
  She told Justin that, through 2025, under the TCJA, his entire itemized deduction    period to incur expenses to use up the
  for state and local taxes — including property tax and either income or sales        previous year’s contribution. In response
  tax — is limited to $10,000 ($5,000 for married taxpayers filing separately). The    to the COVID-19 crisis, the IRS has
  downside of Justin’s raise and bonus was                                             temporarily made FSAs a little more flex-
  that his 2019 state and local tax liability                                          ible. Contact your employer for details.
  exceeded $10,000, so a portion of this                                               If you have an HSA, your FSA is limited
  liability was no longer deductible.                                                  to funding certain permitted expenses.
  The tax advisor went on to explain that the
  limit significantly impacts higher-income
                                                                                       Smaller AMT threat
  taxpayers with large state and local income                                          The top AMT rate is 28%, compared
  tax and/or large property tax bills. She                                             to the top regular ordinary-income tax
  advised that Justin take this into account in                                        rate of 37%. But the AMT rate typically
  his income and deduction timing strategies                                           applies to a higher taxable income base.
  going forward.                                                                       You must pay the AMT if your AMT
                                                                                       liability exceeds your regular tax liability.

percentage of your adjusted gross            If one spouse has high medical            The TCJA substantially increases the
income (AGI), you can claim an               expenses and a relatively lower           AMT exemptions through 2025. (See
itemized deduction for the amount            AGI, filing separately may allow          Chart 8 on page 24.) This means fewer
exceeding that “floor.” This floor           that spouse to exceed the AGI floor       taxpayers will have to pay the AMT. In
can be difficult for higher-income           and deduct some medical expenses          addition, deductions used to calculate
taxpayers to exceed.                         that wouldn’t be deductible if the        regular tax that aren’t allowed under the
                                             couple filed jointly. Warning: Because    AMT can trigger AMT liability, and
The TCJA had reduced the floor from          the AMT exemption for separate            there aren’t as many differences between
10% to 7.5% for 2017 and 2018, and           returns is considerably lower than        what’s deductible for AMT purposes
last year the 7.5% floor was extended        the exemption for joint returns, filing   and regular tax purposes. (See Chart 2
to 2019 and 2020. But it will return to      separately to exceed the floor could      on page 4.) This also reduces AMT risk.
10% for 2021 unless Congress extends         trigger the AMT.                          However, AMT will remain a threat for
the lower floor again. (Check with your                                                some higher-income taxpayers.
tax advisor for the latest information.)     You may be able to save taxes without
                                             having to worry about the medical         So before timing your income and
Eligible expenses may include                expense deduction floor by contributing   expenses, determine whether you’re
health insurance premiums,                   to one of these accounts:                 already likely to be subject to the
long-term-care insurance premiums                                                      AMT — or whether the actions
(limits apply), medical and dental           HSA. If you’re covered by a qualified     you’re considering might trigger it.
services, and prescription drugs.            high deductible health plan, you          In addition to deduction differences,
Mileage driven for health care pur-          can contribute pretax income to an        some income items might trigger or
poses also can be deducted — at 17           employer-sponsored Health Savings         increase AMT liability:
cents per mile for 2020.                     Account — or make deductible
                                             contributions to an HSA you set up        y	Long-term capital gains and qualified
Consider bunching elective medical           yourself — up to $3,550 for self-only        dividend income,
procedures (and any other services and       coverage and $7,100 for family
                                                                                       y	Accelerated depreciation adjustments
purchases whose timing you can control       coverage for 2020 (plus $1,000 if
                                                                                          and related gain or loss differences
without negatively affecting your or         you’re age 55 or older). HSAs can
                                                                                          when assets are sold, and
your family’s health) into alternating       bear interest or be invested, growing
years if it would help you exceed the        tax-deferred similar to an IRA.           y	Tax-exempt interest on certain
applicable floor and you’d have enough       Withdrawals for qualified medical            private-activity municipal bonds.
total itemized deductions to benefit         expenses are tax-free, and you can           (For an exception, see the warning
from itemizing.                              carry over a balance from year to year.      on page 11.)
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
4 Income & Deductions

                Finally, in certain situations exercising
                incentive stock options (ISOs) can           CHART 2     What itemized deductions are
                trigger significant AMT liability. (See                  also deductible for AMT purposes?
                the warning at the top of page 7.)
                                                                         Expense               Regular tax   AMT        For more information
                Avoiding or reducing AMT                                                                            See “Impact of the TCJA on
                                                              State and local income tax           n
                With proper planning, you may be                                                                    timing strategies” on page 2.
                able to avoid the AMT, reduce its             Property tax
                                                                                                                    See “Home-related
                                                                                                   n                deductions” on page 12.
                impact or even take advantage of its
                lower maximum rate:                                                                                 See “Home-related
                                                              Mortgage interest                    n          n     deductions” on page 12.
                If you could be subject to the AMT            Interest on home equity debt
                this year … consider accelerating                                                                   See “Home-related
                                                              used to improve your principal       n          n     deductions” on page 12.
                income into this year, which may              residence or second residence
                allow you to benefit from the lower                                                                 See Case Study 5 on
                maximum AMT rate. And deferring               Investment interest                  n          n     page 11.
                expenses you can’t deduct for AMT
                                                                                                                    See “Tax-advantaged saving
                purposes may allow you to preserve            Medical expenses                     n          n     for health care” on page 2.
                those deductions (but watch out for
                the annual limit on the state and             Charitable contributions             n          n     See page 16.
                local tax deduction). If you also
                defer expenses you can deduct for           more per biweekly pay period aren’t          Additional 0.9% Medicare tax
                AMT purposes, the deductions may            eligible. As of this writing, there          Another payroll tax that higher-
                become more valuable because of             are many open questions about the            income taxpayers must be aware of
                the higher maximum regular tax              deferral. Contact your tax advisor           is the additional 0.9% Medicare tax.
                rate. Finally, carefully consider the       for the latest information.                  It applies to FICA wages and net
                tax consequences of exercising ISOs.
                                                                                                         self-employment income exceeding
                                                            Self-employment taxes                        $200,000 per year ($250,000 if married
                If you could be subject to the AMT          If you’re self-employed, you pay             filing jointly and $125,000 if married
                next year … consider taking the             both the employee and employer               filing separately).
                opposite approach. For instance, defer      portions of payroll taxes on your
                income to next year, because you’ll         self-employment income. The                  If your wages or self-employment
                likely pay a relatively lower AMT           employer portion (6.2% for Social            income varies significantly from year
                rate. Also, before year end consider        Security tax and 1.45% for Medicare          to year or you’re nearing the threshold
                selling any private-activity municipal      tax) is deductible above the line.           for triggering the additional Medicare
                bonds whose interest could be subject       You also may be eligible for some            tax, income timing strategies may help
                to the AMT.                                 COVID-19 payroll tax relief. (See            you avoid or minimize it. For example,
                                                            “What’s new!” at right.)                     if you’re an employee, perhaps you
                Also be aware that, in certain circum-                                                   can time when you receive a bonus
                stances, you may be entitled to an          As a self-employed taxpayer, you may         or exercise stock options. If you’re
                AMT credit.                                 benefit from other above-the-line            self-employed, you may have flexibility
                                                            deductions as well. You can deduct           on when you purchase new equipment
                Payroll taxes                               100% of health insurance costs               or invoice customers. If you’re an
                In addition to income tax, you must         for yourself, your spouse and your           S corporation shareholder-employee,
                pay Social Security and Medicare            dependents, up to your net self-             you might save tax by adjusting how
                taxes on earned income, such as             employment income. You also can              much you receive as salary vs. distribu-
                salary and bonuses. The 12.4% Social        deduct contributions to a retirement         tions. (See “Owner-employees” at right.)
                Security tax applies only up to the         plan and, if you’re eligible, an HSA
                Social Security wage base of $137,700       for yourself. And you might be able          Also consider the withholding rules.
                for 2020. All earned income is subject      to deduct home office expenses. (See         Employers must withhold the addi-
                to the 2.9% Medicare tax. Both              page 12.) Above-the-line deductions          tional tax beginning in the pay period
                taxes are split equally between the         are particularly valuable because            when wages exceed $200,000 for the
                employee and the employer.                  they reduce your AGI and, depend-            calendar year — without regard to an
                                                            ing on the specific deduction, your          employee’s filing status or income from
                Also, an Aug. 8 presidential mem-           modified AGI (MAGI), which are               other sources. So your employer might
                orandum offers a deferral of the            the triggers for certain additional          withhold the tax even if you aren’t liable
                employee share of Social Security           taxes and the phaseouts of many              for it — or it might not withhold the tax
                taxes, but those earning $4,000 or          tax breaks.                                  even though you are liable for it.
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
Income & Deductions 5

If you don’t owe the tax but your            the income isn’t distributed to you.        C corporations. Only income you
employer is withholding it, you can          But such income may not be subject          receive as salary is subject to payroll
claim a credit on your 2020 income tax       to self-employment taxes if you’re a        taxes and, if applicable, the 0.9%
return. If you do owe the tax but your       limited partner or the LLC member           Medicare tax. Nonetheless, you may
employer isn’t withholding it, consider      equivalent. Check with your tax             prefer to take more income as salary
filing a W-4 form to request additional      advisor on whether the additional 0.9%      (which is deductible at the corporate
income tax withholding, which can be         Medicare tax on earned income or the        level) as opposed to dividends (which
used to cover the shortfall and avoid        3.8% NIIT (see page 11) will apply.         aren’t deductible at the corporate level
interest and penalties. Or you can                                                       yet are still taxed at the shareholder
make estimated tax payments.                 S corporations. Only income you             level and could be subject to the 3.8%
                                             receive as salary is subject to payroll     NIIT) if the overall tax paid by both
Owner-employees                              taxes and, if applicable, the 0.9%          the corporation and you would be less.
There are special considerations if          Medicare tax. To reduce these taxes,
you’re a business owner who also             you may want to keep your salary            Warning: The IRS scrutinizes corporate
works in the business, depending on          relatively — but not unreasonably —         payments to shareholder-employees
its structure:                               low and increase the income that is         for possible misclassification, so tread
                                             taxed to you through your Schedule K-1      carefully.
Partnerships and limited liability           by virtue of your share of the earnings
companies. Generally, all trade or           from the business. That income isn’t        Estimated payments
business income that flows through to        subject to the corporate level tax or       and withholding
you for income tax purposes is subject       the 0.9% Medicare tax and, typically,       You can be subject to penalties if you
to self-employment taxes — even if           is not subject to the 3.8% NIIT.            don’t pay enough tax during the year
                                                                                         through estimated tax payments and
                                                                                         withholding. Here are some strategies
 WHAT’S
            COVID-19 payroll tax relief for the self-employed                            to help avoid underpayment penalties:
 NEW!

                                                                                         Know the minimum payment rules.
                               To help the self-employed — and employers — during
                                                                                         For you to avoid penalties, your
                               the COVID-19 crisis, the CARES Act allows the pay-
                                                                                         estimated payments and withholding
                               ment of the employer share (6.2% of wages) of the
                                                                                         must equal at least 90% of your tax
                               Social Security payroll tax to be deferred. Taxpayers
                                                                                         liability for 2020 or 110% of your
                               can pay the tax over the next two years, with the first
                                                                                         2019 tax (100% if your 2019 AGI
                               half due by Dec. 31, 2021, and the second half due
                                                                                         was $150,000 or less or, if married
                               by Dec. 31, 2022. Be aware that, as of this writing,
                                                                                         filing separately, $75,000 or less).
                               it appears that the deferral of the employee share of
                               Social Security taxes noted under “Payroll taxes” at
                               left isn’t available to the self-employed. Check with
                                                                                         Use the annualized income installment
                               your tax advisor for the latest information.
                                                                                         method. This method often benefits
                                                                                         taxpayers who have large variability in
  If you have employees, additional payroll tax breaks may be available to you:          income from month to month due to
                                                                                         bonuses, investment gains and losses, or
  Payroll tax credit. Under the CARES Act, this credit is generally available to         seasonal income (at least if it’s skewed
  employers whose operations have been fully or partially suspended because of a         toward the end of the year). Annualizing
  COVID-19-related governmental shutdown order or whose gross receipts have              computes the tax due based on income,
  dropped more than 50% compared to the same quarter in the previous year. The           gains, losses and deductions through
  credit equals 50% of up to $10,000 in compensation, including health care bene-        each estimated tax period.
  fits, paid to an eligible employee after March 12, 2020, through Dec. 31, 2020.
                                                                                         Estimate your tax liability and increase
  Paid leave credit. The Families First Coronavirus Response Act generally               withholding. If you determine you’ve
  requires employers with fewer than 500 employees to provide paid leave in              underpaid, consider having the tax
  certain COVID-19-related situations. Covered employers generally can take a            shortfall withheld from your salary or
  federal payroll tax credit for 100% of the qualified sick and family leave wages       year end bonus by Dec. 31. Because
  they pay each quarter, up to $511 per day for leave taken for the employee’s           withholding is considered to have been
  own illness or quarantine and $200 for leaves taken to care for others.                paid ratably throughout the year, this
                                                                                         is often a better strategy than making
  Additional rules and limits apply to these breaks, and it’s possible they could
                                                                                         up the difference with an increased
  be expanded or extended by the time you’re reading this or that additional
                                                                                         quarterly tax payment, which may
  relief for employers could become available. Check with your tax advisor for
                                                                                         still leave you exposed to penalties for
  the latest information.
                                                                                         earlier quarters.
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
6 Executive Compensation

Smart tax planning for your
exec comp package is critical

                          ompensation may take several           There are some potential disad-            Such a delay will defer income tax
                  C       forms, including salary, fringe
                          benefits and bonuses. If you’re
                                                                 vantages of a Sec. 83(b) election,
                                                                 however. First, prepaying tax in the
                                                                                                            and may allow you to reduce or avoid
                                                                                                            exposure to the additional 0.9%
                an executive or other key employee, you          current year could push you into a         Medicare tax (because the RSUs are
                might receive stock-based compensa-              higher income tax bracket and trigger      treated as FICA income). However,
                tion, such as restricted stock, restricted       or increase your exposure to the           any income deferral must satisfy
                stock units (RSUs) or stock options              additional 0.9% Medicare tax. But          the strict requirements of Internal
                (either incentive or nonqualified).              if your company is in the earlier          Revenue Code Section 409A. Also
                Nonqualified deferred compensation               stages of development, the income          keep in mind that it might be better
                (NQDC) may also be included in your              recognized may be relatively small.        to recognize income now because of
                exec comp package. The tax conse-                                                           the currently low tax rates.
                quences of these types of compensation           Second, any taxes you pay because of
                can be complex — subject to ordinary             the election can’t be refunded if you      Incentive stock options
                income, capital gains, payroll and other         eventually forfeit the stock or sell it    ISOs allow you to buy company
                taxes. So smart tax planning is critical.        at a decreased value. However, you’d       stock in the future (but before a set
                                                                 have a capital loss in those situations.   expiration date) at a fixed price equal
                Restricted stock                                                                            to or greater than the stock’s FMV
                Restricted stock is stock your employer          Third, when you sell the shares, any       at the date of the grant. Thus, ISOs
                grants to you subject to a substantial risk      gain will be included in net investment    don’t provide a benefit until the stock
                of forfeiture. Income recognition is nor-        income and could trigger or increase       appreciates in value. If it does, you
                mally deferred until the stock is no longer      your liability for the 3.8% NIIT. (See     can buy shares at a price below what
                subject to that risk (that is, it’s vested) or   page 11.)                                  they’re then trading for, provided
                you sell it. When the restriction lapses,                                                   you’re eligible to exercise the options.
                you pay taxes on the stock’s fair market         See Case Study 2 for additional
                value (FMV) at your ordinary-income              information, and work with your            ISOs receive tax-favored treatment
                rate. (The FMV will be considered FICA           tax advisor to map out whether the         but must comply with many rules.
                income, so it could trigger or increase          Sec. 83(b) election is appropriate         Here are the key tax consequences:
                your exposure to the additional 0.9%             for your situation.
                Medicare tax. See page 4.)                                                                  y	You owe no tax when ISOs are
                                                                 RSUs                                          granted.
                But you can instead make a                       RSUs are contractual rights to
                                                                                                            y	You owe no regular income tax
                Section 83(b) election to recognize              receive stock, or its cash value,
                                                                                                               when you exercise the ISOs.
                ordinary income when you receive the             after the award has vested. Unlike
                stock. This election, which you must             restricted stock, RSUs aren’t eligible     y	If you sell the stock after holding
                make within 30 days after receiving the          for the Sec. 83(b) election. So               the shares at least one year from the
                stock, allows you to convert potential           there’s no opportunity to convert             exercise date and two years from
                future appreciation from ordinary income         ordinary income into capital gains.           the grant date, you pay tax on the
                to long-term capital gains income and                                                          sale at your long-term capital gains
                defer it until the stock is sold.                But they do offer a limited ability           rate. You also may owe the NIIT.
                                                                 to defer income taxes: Unlike
                                                                                                            y	If you sell the stock before long-term
                The election can be beneficial if the            restricted stock, which becomes
                                                                                                               capital gains treatment applies, a
                income at the grant date is negligible           taxable immediately upon vesting,
                                                                                                               “disqualifying disposition” occurs and
                or the stock is likely to appreciate             RSUs aren’t taxable until the
                                                                                                               any gain is taxed as compensation at
                significantly before income would                employee actually receives the
                                                                                                               ordinary-income rates. (Disqualified
                otherwise be recognized. And with                stock. So rather than having the
                                                                                                               dispositions aren’t, however, subject
                ordinary-income rates now especially             stock delivered immediately upon
                                                                                                               to FICA and Medicare tax, including
                low under the TCJA, it might be a                vesting, you may be able to arrange
                                                                                                               the additional 0.9% Medicare tax.)
                good time to recognize income.                   with your employer to delay delivery.
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
Executive Compensation 7

Warning: If you don’t sell the stock         gains rate and the NIIT. See Case            favor highly compensated employees,
in the year of exercise, a tax “prefer-      Study 2 for additional information           but plan funding isn’t protected from
ence” item is created for the difference     and, with your tax advisor, evaluate         the employer’s creditors. (For more on
between the stock’s FMV and the              the risks and crunch the numbers to          401(k)s, see page 20.)
exercise price (the “bargain element”)       determine the best strategy for you.
that can trigger the AMT. A future                                                        One important NQDC tax issue is
AMT credit, however, should mitigate         Nonqualified stock options                   that payroll taxes (see page 4) are
this AMT hit. Plus, you may now be at        The tax treatment of NQSOs is different      generally due once services have been
lower AMT risk because of the higher         from the tax treatment of ISOs: NQSOs        performed and there’s no longer a
AMT exemption and exemption                  create compensation income (taxed at         substantial risk of forfeiture — even
phaseout range under the TCJA. (See          ordinary-income rates) on the bargain        though compensation may not be paid
Chart 8 on page 24.) Consult your tax        element when exercised (regardless of        or recognized for income tax purposes
advisor because the rules are complex.       whether the stock is held or sold imme-      until much later. So your employer
                                             diately), but they don’t create an AMT       may withhold your portion of the
If you’ve received ISOs, plan carefully      preference item.                             payroll taxes from your salary or ask
when to exercise them and whether to                                                      you to write a check for the liability.
immediately sell shares received from        You may need to make estimated tax           Or it may pay your portion, in which
an exercise or hold them. Waiting            payments or increase withholding to          case you’ll have additional taxable
to exercise ISOs until just before the       fully cover the tax on the exercise.         income. Warning: The additional
expiration date (when the stock value        Keep in mind that an exercise could          0.9% Medicare tax could also apply.
may be the highest, assuming the stock       trigger or increase exposure to top tax
is appreciating) and holding on to the       rates, the additional 0.9% Medicare          Keep in mind that the rules for NQDC
stock long enough to garner long-            tax and the NIIT.                            plans are tighter than they once were,
term capital gains treatment often is                                                     and the penalties for noncompliance
beneficial. But there’s also market risk                                                  can be severe: You could be taxed on
                                             NQDC plans
to consider. Plus, acting earlier can be                                                  plan benefits at the time of vesting, and
advantageous in several situations:          These plans pay executives in the future     a 20% penalty and potential interest
                                             for services to be currently performed.      charges also could apply. So check
y	Exercise early to start the holding       They differ from qualified plans, such as    with your employer to make sure it’s
   period so you can sell and receive        401(k)s, in several ways. For example,       addressing any compliance issues.
   long-term capital gains treatment         unlike 401(k) plans, NQDC plans can
   sooner.
y	Exercise when the bargain element          CASE        Some stock-based compensation
   is small or when the market price is       STUDY 2     may qualify for TCJA tax deferral
   close to bottoming out to reduce or
                                                                                                Mario was about to receive some
   eliminate AMT liability.
                                                                                                stock-based compensation from
y	Exercise annually so you can buy                                                             his employer, so he contacted
   only the number of shares that will                                                          his tax advisor to find out what
   achieve a breakeven point between                                                            the tax consequences would be.
   the AMT and regular tax and                                                                  His advisor explained that the tax
   thereby incur no additional tax.                                                             treatment would depend on the
                                                                                                type of stock-based compensa-
y	Sell in a disqualifying disposition and                                                      tion. For example, Mario might
   pay the higher ordinary-income rate                                                          be able to take advantage of
   to avoid the AMT on potentially                                                              the Section 83(b) election. (See
   disappearing appreciation.                                                                   “Restricted stock” at left.) Or he
                                                                                                might be eligible for a tax break
On the negative side, exercising early                                                          under the TCJA.
accelerates the need for funds to buy
the stock, exposes you to a loss if the                                                            The TCJA break allows for the
shares’ value drops below your exercise                                                            deferral of tax on stock-based
                                               compensation in certain circumstances. Generally, it gives taxpayers the oppor-
cost, and may create a tax cost if the
                                               tunity to match the taxation of restricted stock and stock options with the timing
preference item from the exercise
                                               of the sale of the stock. It’s intended for situations in which there is no ready
generates an AMT liability.
                                               market for the sale of the stock.

The timing of ISO exercises also could         The availability of the deferral opportunity is limited, however. It generally will
positively or negatively affect your lia-      apply only if at least 80% of full-time employees are covered by the stock-based
bility for the higher ordinary-income          compensation plan.
tax rates, the 20% long-term capital
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
8 Investing

Uncertainty further complicates
tax planning for investments

                       ax treatment of investments          Being tax-smart with losses                          against ordinary income (such as wages,
                T      varies dramatically based
                       on factors such as type of
                                                            Losses aren’t truly losses until they’re
                                                            realized — that is, generally until you
                                                                                                                 self-employment and business income,
                                                                                                                 interest, dividends, and taxable retire-
              investment, type of income it produces,       sell the investment for less than what               ment plan distributions). But you can
              how long you’ve held it and whether           you paid for it. So while it’s distressing           carry forward excess losses until death.
              any special limitations or breaks apply.      to see an account statement that shows
              On top of that, economic uncertainty          a large loss, the loss won’t affect your             If you don’t have enough gains to absorb
              has made tax planning for investments         current tax situation as long as you still           losses, you could be left with losses in
              especially challenging this year.             own the investment.                                  excess of the annual ordinary-income
                                                                                                                 deduction limit. So think twice before
              And there are many additional factors to      Realized capital losses are netted against           selling an investment at a loss. After
              evaluate before deciding whether to sell      realized capital gains to determine                  all, if you hold on to the investment,
              or hold an investment, such as invest-        capital gains tax liability. If net losses           it may recover the lost value. In fact,
              ment goals, time horizon, risk tolerance,     exceed net gains, you can deduct only                a buy-and-hold strategy works well for
              factors related to the investment itself,     $3,000 ($1,500 for married taxpayers                 many long-term investors because it can
              fees and charges that apply to buying and     filing separately) of losses per year                minimize the effects of market volatility.
              selling securities, and your need for cash.
              But taxes are still important to consider.
                                                             CHART 3
                                                                             What’s the maximum 2020 capital gains tax rate?
              Capital gains tax and timing
              Although time, not timing, is gener-                                   Type of gain                                            Rate1
              ally the key to long-term investment                                                                                  Taxpayer’s ordinary-
              success, timing can have a dramatic             Short-term (assets held 12 months or less)
                                                                                                                                      income tax rate
              impact on the tax consequences of
                                                              Long-term (assets held more than 12 months)                                    15%
              investment activities. Your marginal
              long-term capital gains rate can be as          Some key exceptions
              much as 20 percentage points lower              Long-term gain of certain higher-income taxpayers                             20%2
              than your ordinary-income tax rate.
                                                              Most long-term gain that would be taxed at 10% or
                                                                                                                                              0%
                                                              12% based on the taxpayer’s ordinary-income rate
              The long-term capital gains rate applies
              to investments held for more than 12            Long-term gain on collectibles, such as artwork
                                                                                                                                             28%
                                                              and antiques
              months. The applicable rate depends
              on your income level and the type of            Long-term gain attributable to certain recapture of
                                                                                                                                             25%
              asset you’ve sold. (See Chart 3.)               prior depreciation on real property
                                                              Gain on qualified small business (QSB) stock held
              Because of TCJA-related changes to              more than 5 years
              the brackets, through 2025, the top                 n   	Acquired before Feb. 18, 2009                                       14%3
              long-term gains rate of 20% kicks
                                                                  n   	Acquired on or after Feb. 18, 2009, and before
              in before the top ordinary-income                                                                                              7%4
                                                                        Sept. 28, 2010
              rate does. (See Chart 8 on page 24.)
              Higher rates still apply to certain                 n   	Acquired on or after Sept. 28, 2010                                   0%
              types of assets. (See Chart 3.)                 	In addition, the 3.8% net investment income tax (NIIT) applies to net investment income to the
                                                              1

                                                               extent that modified adjusted gross income (MAGI) exceeds $200,000 (singles and heads of
                                                               households), $250,000 (married filing jointly) or $125,000 (married filing separately).
              Holding on to an investment until
                                                              	The 20% rate applies only to those with taxable income exceeding $441,450 (singles), $469,050
                                                              2
              you’ve owned it more than one year               (heads of households), $496,600 (joint filers), or $248,300 (separate filers).
              may help substantially cut tax on any           	Effective rate based on a 50% exclusion from a 28% rate.
                                                              3

              gain. Keeping it even longer can also           	Effective rate based on a 75% exclusion from a 28% rate.
                                                              4

              make tax sense.
Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
Investing 9

                                                                                         Mutual funds
 CASE
 STUDY 3     Use capital losses to absorb unrecognized gains                             Investing in mutual funds is an easy
                                                                                         way to diversify your portfolio. But
  Marisa’s year-to-date net                                                              beware of the tax pitfalls.
  realized losses are $53,000.
  Her portfolio includes                                                                 First, mutual funds with high turnover
  $100,000 of stock that                                                                 rates can create income that’s taxed
  she paid only $50,000 for.                                                             at ordinary-income rates. Choosing
  Marisa has been thinking                                                               funds that provide primarily long-term
  about selling it to diversify                                                          gains can save you more tax dollars
  her portfolio and because                                                              because of the lower long-term rates.
  year-to-date the stock had
  dropped from $130,000 to                                                               Second, earnings on mutual funds
  $100,000 in value and she’s                                                            are typically reinvested. Unless you
  not confident it will recover.
                                                                                         or your investment advisor increases
  But she’s been concerned                                                               your basis accordingly, you may report
  about the capital gains tax.                                                           more gain than required when you sell
                                                                                         the fund. Brokerage firms are required
  Her tax advisor suggests                                                               to track (and report to the IRS) your
  that now might be a good                                                               cost basis in mutual funds acquired
  time to sell the stock because her $50,000 gain would essentially be tax-free:         during the tax year.
  The gain would absorb $50,000 of losses, leaving Marisa with a $3,000 net
  loss, the maximum that she could use to offset ordinary income.                        Third, buying equity mutual fund
                                                                                         shares late in the year can be costly
Of course, an investment might con-           Fortunately, there are ways to avoid       taxwise. Such funds often declare
tinue to lose value. That’s one reason        triggering the wash sale rule and          a large capital gains distribution at
why tax considerations shouldn’t              still achieve your goals. For example,     year end, which is a taxable event.
be the primary driver of investment           you can:                                   If you own the shares on the distri-
decisions. If you’re ready to divest                                                     bution’s record date, you’ll receive
yourself of a poorly performing stock         y	Sell the security and immediately       and be taxed on the full distribution
because, for example, you don’t think            buy securities of a different company   amount even if it includes significant
its performance will improve or your             in the same industry or shares in a     gains realized by the fund before you
investment objective or risk tolerance           mutual fund that holds securities       owned the shares. And you’ll pay tax
has changed, don’t hesitate solely for           much like the ones you sold,            on those gains in the current year —
tax reasons.                                                                             even if you reinvest the distribution.
                                              y	Sell the security and wait 31 days
                                                 to repurchase the same security, or     Small business stock
Plus, building up losses for future
use could be beneficial. This may             y	Before selling the security, purchase   By purchasing stock in certain small
be especially true if you have a large           additional shares of that security      businesses, you can diversify your
investment portfolio, real estate                equal to the number you want to         portfolio. You also may enjoy prefer-
holdings or a closely held business              sell at a loss, and then wait 31 days   ential tax treatment:
that might generate substantial                  to sell the original portion.
future gains, or if tax rates increase.                                                  Conversion of capital loss to
                                              Alternatively, you can do a bond swap,     ordinary loss. If you sell qualifying
Finally, remember that capital gains          where you sell a bond, take a loss and     Section 1244 small business stock at
distributions from mutual funds can           then immediately buy another bond          a loss, you can treat up to $50,000
also absorb capital losses.                   of similar quality and duration from a     ($100,000, if married filing jointly)
                                              different issuer. Generally, the wash      as an ordinary, rather than a capital,
Wash sale rule                                sale rule doesn’t apply because the        loss — regardless of your holding
If you want to achieve a tax loss with        bonds aren’t considered substantially      period. This means you can use it to
minimal change in your portfolio’s            identical. Thus, you can achieve a         offset ordinary income, reducing your
asset allocation, consider the wash sale      tax loss with virtually no change in       tax by as much as 37% of this portion
rule. It prevents you from taking a loss      economic position.                         of the loss. Sec. 1244 applies only if
on a security if you buy a substantially                                                 total capital invested isn’t more than
identical security (or an option to buy       Warning: You can’t avoid the wash          $1 million.
such a security) within 30 days before        sale rule by selling stock at a loss in
or after you sell the security that created   a taxable account and purchasing           Tax-free gain rollovers. If within 60
the loss. You can recognize the loss only     the same stock within 30 days in a         days of selling qualified small business
when you sell the replacement security.       tax-advantaged retirement account.         (QSB) stock you buy other QSB stock
10 Investing

                                                                                                          claim will be able to withstand IRS
                CASE                                                                                      scrutiny, carefully track and document
                STUDY 4     How to qualify for the 0% capital gains rate
                                                                                                          your time. Contemporaneous record-
                                                                                                          keeping is better than records that are
                                                           Faced with a long-term capital gains
                                                                                                          created after the fact.
                                                           tax rate of 23.8% (20% for the top tax
                                                           bracket, plus the 3.8% NIIT), Michael
                                                           and Jennifer decide to give some               If you don’t pass the material partici-
                                                           appreciated stock to their adult son,          pation test, consider:
                                                           Ian. Just out of college and making only
                                                           enough from his entry-level job to leave       Increasing your involvement. If you
                                                           him with $25,000 in taxable income,            can exceed 500 hours, the activity
                                                           Ian falls into the 12% ordinary-income         no longer will be subject to passive
                                                           tax bracket and the 0% long-term               activity rules.
                                                           capital gains bracket.
                                                                                                          Grouping activities. You may be able
                 However, the 0% rate applies only to the extent that capital gains “fill up” the gap     to group certain activities together
                 between Ian’s taxable income and the top end of the 0% bracket. For 2020, the            to be treated as one activity for tax
                 0% bracket for singles tops out at $40,000 (just $125 less than the top of the
                                                                                                          purposes and exceed the 500-hour
                 12% ordinary-income bracket). So if Ian sells the stock his parents transferred
                                                                                                          threshold. But the rules are complex,
                 to him and his gains are $15,000, the entire amount will qualify for the 0% rate.
                                                                                                          and there are potential downsides
                 The sale will be tax-free vs. the $3,570 Michael and Jennifer would have owed
                 had they sold the stock themselves.
                                                                                                          to consider.

                 Warning: If Ian had been subject to the “kiddie tax” (see page 18), the results          Looking at other activities. If you
                 would have been quite different. It’s also important to consider any gift tax con-       have passive losses, one option is to
                 sequences before transferring stock. (See page 22.)                                      limit your participation in another
                                                                                                          activity that’s generating income, so
                                                                                                          that you don’t meet the 500-hour test.
               with the proceeds, you can defer the         Keep in mind that all three of these          Another is to invest in an additional
               tax on your gain until you dispose of        tax benefits are subject to additional        income-producing trade or business
               the new stock. The rolled-over gain          requirements and limits. Consult your         that will be passive to you. Under
               reduces your basis in the new stock. For     tax and financial advisors to be sure         both strategies, you’ll have passive
               determining long-term capital gains          an investment in small business stock         income that can absorb some or all
               treatment, the new stock’s holding           is right for you.                             of your passive losses.
               period includes the holding period
               of the stock you sold. To be a QSB, a        Passive activities                            Disposing of the activity. This
               business must be engaged in an active        If you’ve invested in a trade or business     generally allows you to deduct all
               trade or business and must not have          in which you don’t materially partic-         passive losses — including any loss
               assets that exceed $50 million, among        ipate and where income or loss flows          on disposition (subject to basis and
               other requirements.                          through to your tax return, remember          capital loss limitations). But, again,
                                                            the passive activity rules. Why? Passive      the rules are complex.
               Exclusion of gain. Generally, tax-           activity income may be subject to the
               payers selling QSB stock are allowed         3.8% NIIT (see page 11), and passive          Even if you do pass the material
               to exclude up to 100% of their gain if       activity losses generally are deductible      participation test, be aware that your
               they’ve held the stock for more than         only against income from other passive        loss deduction might be affected by
               five years. But, depending on the            activities. You can carry forward             the TCJA’s rules for deducting business
               acquisition date, the exclusion may be       disallowed losses to the following year,      losses. (See “What’s new!” on page 14.)
               less: The exclusion is 75% for stock         subject to the same limits.
               acquired on or after Feb. 18, 2009, and                                                    Income investments
               before Sept. 28, 2010, and 50% for           To avoid passive activity treatment,          Qualified dividends are taxed at the
               stock acquired before Feb. 18, 2009.         you must “materially participate” in          favorable long-term capital gains
                                                            the activity, which typically means you       tax rate rather than at your higher
               When the exclusion is less than 100%,        must participate in the trade or business     ordinary-income tax rate. Interest
               the taxable portion of any QSB gain          more than 500 hours during the year           income, however, generally is taxed at
               will be subject to the lesser of your        or demonstrate that your involvement          ordinary-income rates.
               ordinary-income rate or 28%, rather          constitutes substantially all of the
               than the normal long-term gains rate.        participation in the activity. But there      So stocks that pay qualified dividends
               (See Chart 3 on page 8.) Thus, if the        are other ways to meet the material           may be more attractive taxwise than
               28% rate and the 50% exclusion apply,        participation test. Plus, there are special   other income investments, such as
               the effective rate on the QSB gain will      rules that apply to real estate. (See         CDs and taxable bonds. But there are
               be 14% (28% × 50%).                          page 13.) To help ensure your hours           exceptions.
Investing 11

Some dividends, for example, are sub-         y	Bonds (except U.S. savings bonds)         The fact that a bond is exempt from
ject to ordinary-income rates. These             with original issue discount (OID)        federal tax doesn’t necessarily make it a
include certain dividends from:                  build up “interest” as they rise toward   better choice than a comparable taxable
                                                 maturity. You’re generally considered     bond. Municipal bonds, for example,
y	Real estate investment trusts                 to earn a portion of that interest        typically offer lower yields than compa-
   (REITs),                                      annually — even though the bonds          rable corporate bonds. To make a fair
                                                 don’t pay this interest annually —        comparison, you need to calculate the
y	Regulated investment companies
                                                 and you must pay tax on it.               tax-equivalent yield — which incor-
   (RICs),
                                                                                           porates tax savings into the municipal
                                              y	Interest on U.S. government bonds
y	Money market mutual funds, and                                                          bond’s yield — using this formula:
                                                 is taxable on federal returns but
y	Certain foreign investments.                  exempt by federal law on state and
                                                                                           Tax-equivalent yield = actual yield /
                                                 local returns.
                                                                                           (1 – your marginal tax rate).
The tax treatment of bond income
                                              y	Interest on state and local govern-
varies. For example:
                                                 ment bonds is excludable on federal       But you also need to consider factors
                                                 returns. If the bonds were issued in      such as risk and how well each bond
y	Corporate bond interest is fully              your home state, interest also may        will help achieve your overall invest-
   taxable for federal and state                 be excludable on your state return,       ment goals.
   purposes.                                     depending on the state.
                                                                                           Warning: Tax-exempt interest from
 CASE                                                                                      private-activity municipal bonds can
 STUDY 5     Can you deduct investment interest expense?                                   trigger or increase AMT liability.
                                                                                           However, any income from tax-exempt
  Frank borrowed to make some                                                              bonds issued in 2009 and 2010 (along
  investments this year, and he was                                                        with 2009 and 2010 re-fundings of
  wondering if the interest would be                                                       bonds issued after Dec. 31, 2003, and
  deductible. So he consulted his                                                          before Jan. 1, 2009) is excluded from
  tax advisor.
                                                                                           the AMT. And AMT is less of a risk
  She told him that investment                                                             for most taxpayers now. (See page 3.)
  interest expense — interest on
  debt used to buy assets held for                                                         3.8% NIIT
  investment, such as margin debt                                                          Taxpayers with modified adjusted
  used to buy securities — generally                                                       gross income (MAGI) over $200,000
  is deductible for both regular tax                                                       ($250,000 if married filing jointly and
  and alternative minimum tax (see                                                         $125,000 if married filing separately)
  page 3) purposes. But special                                                            may owe the net investment income
  rules apply.                                                                             tax (NIIT) on top of whatever other
  First, Frank’s investment interest
                                                                                           tax they owe on their investment
  expense deduction would be                                                               income. The NIIT equals 3.8% of the
  limited to his net investment                                                            lesser of net investment income or the
  income, which, for the purposes                                                          amount by which MAGI exceeds the
  of this deduction, generally                                                             applicable threshold.
  includes taxable interest, nonqualified dividends and net short-term capital gains
  (but not long-term capital gains), reduced by other investment expenses. Any             Net investment income can include
  disallowed interest expense is carried forward, and Frank can deduct it in a later       capital gains, dividends, interest, passive
  year against net investment income.                                                      business income, rental income and
                                                                                           other investment-related income. But
  If his interest expense exceeds his net investment income, Frank may elect to            it doesn’t include business or self-rental
  treat all or a portion of his net long-term capital gains or qualified dividends as      income from an active trade or business.
  investment income in order to deduct more of his investment interest expense.
  But if he does, that portion of the long-term capital gain or dividend will be taxed
                                                                                           Many of the strategies that can help
  at ordinary-income rates.
                                                                                           you save or defer income tax on your
  Frank’s advisor also explained that payments a short seller makes to the stock           investments can also help you avoid
  lender in lieu of dividends may be deductible as investment interest expense.            or defer NIIT liability. And because
  But interest on debt used to buy securities that pay tax-exempt income, such             the threshold for the NIIT is based
  as municipal bonds, isn’t deductible. Finally, she told Frank to keep in mind            on MAGI, strategies that reduce your
  that passive interest expense — interest on debt incurred to fund a passive              MAGI — such as making retirement
  activity — becomes part of his overall passive activity income or loss, subject          plan contributions (see page 20) —
  to limitations. (See page 10.)                                                           could also help you avoid or reduce
                                                                                           NIIT liability.
12 Real Estate

Make the most of tax breaks for
your home and other real estate

                          here are many ways you can         Home office deduction. Under the              depreciate the portion of their home
                   T      maximize the tax benefits
                          associated with owning a
                                                             TCJA, employees can no longer deduct
                                                             home office expenses, because of the
                                                                                                           that’s used as an office, they can claim
                                                                                                           mortgage interest, property taxes and
                 principal residence, vacation home or       suspension of miscellaneous deductions        casualty losses as itemized deductions to
                 rental property. The TCJA has limited       subject to the 2% of adjusted gross           the extent otherwise allowable, without
                 certain breaks, but the CARES Act           income (AGI) floor. (See page 2.) But         needing to apportion them between
                 provides some relief. Tax planning is       the self-employed can still claim the         personal and business use of the home.
                 also important if you’d like to sell your   deduction, as long as their home office
                 home or other real estate this year.        is their principal place of business (or      Home rental rules
                                                             used substantially and regularly to           If you rent out all or a portion of your
                 Home-related deductions                     conduct business) and that’s the only         principal residence or second home
                 Consider these itemized deductions in       use of the space.                             for less than 15 days, you don’t have to
                 your tax planning:                                                                        report the income. But expenses directly
                                                             They can deduct from their self-              associated with the rental, such as adver-
                 Property tax deduction. Under the           employment income a portion of their          tising and cleaning, won’t be deductible.
                 TCJA, through 2025, the property            mortgage interest, property taxes,
                 tax deduction is subject to a $10,000       insurance, utilities and certain other        If you rent out your principal residence
                 limit ($5,000 if you’re married filing      expenses, and the depreciation allocable      or second home for 15 days or more,
                 separately) on combined deductions          to the space. Or they can use the             you’ll have to report the income. But you
                 for state and local taxes (SALT).           simplified method for calculating the         may be entitled to deduct some or all of
                 (See page 2 for more details.)              deduction — $5 per square foot for up         your rental expenses — such as utilities,
                 Higher-income taxpayers owning              to 300 square feet. Although taxpayers        repairs, insurance and depreciation.
                 valuable homes in high-property-tax         using this method won’t be able to            Exactly what you can deduct depends on
                 locations have seen a huge drop in
                 the federal tax benefit they receive
                 from their property tax payments.            WHAT’S     CARES Act QIP correction
                                                              NEW!
                                                                         increases deductions — retroactively
                 Mortgage interest deduction. You
                                                               Prior to the TCJA, qualified retail improvement property, restaurant property
                 generally can deduct interest on mort-
                                                               and leasehold improvement property were depreciated over 15 years under the
                 gage debt incurred to purchase, build
                                                               modified accelerated cost recovery system (MACRS). The TCJA classifies all of
                 or improve your principal residence
                                                               these property types as qualified improvement property (QIP).
                 and a second residence. Points paid
                 related to your principal residence also      Congress intended QIP placed in service after 2017 to have a 15-year MACRS
                 may be deductible. Through 2025, the          recovery period and, in turn, qualify for 100% bonus depreciation. Bonus depre-
                 TCJA reduces the mortgage debt limit          ciation is additional first-year depreciation of 100% for qualified property placed
                 from $1 million to $750,000 for debt          in service through Dec. 31, 2022. For 2023 through 2026, bonus depreciation
                 incurred after Dec. 15, 2017 ($500,000        is scheduled to be gradually reduced.
                 and $375,000, respectively, for separate
                 filers), with some limited exceptions.        But the statutory language didn’t define QIP as 15-year property. So QIP defaulted
                                                               to a 39-year recovery period, making it ineligible for bonus depreciation.
                 Home equity debt interest deduction.
                 Through 2025, the TCJA effectively            The CARES Act corrected this drafting error. Taxpayers that have made qualified
                 limits the home equity interest deduction     improvements during the past two years can claim an immediate tax refund for the
                 to debt that would qualify for the home       bonus depreciation they missed. Taxpayers investing in QIP in 2020 and beyond also
                 mortgage interest deduction. (Under           can claim bonus depreciation going forward, according to the phaseout schedule. In
                 pre-TCJA law, interest was deductible         some cases, however, it might be more beneficial to claim depreciation over 15 years.
                 on up to $100,000 of home equity debt
                                                               Warning: Under the TCJA, real estate businesses that elect to deduct 100% of
                 used for any purpose, such as to pay off
                                                               their business interest are ineligible for bonus depreciation.
                 credit card debt or to buy a car.)
Real Estate 13

whether the home is classified as a rental
property for tax purposes (based on the        WHAT’S      CARES Act temporarily eases
                                               NEW!
amount of personal vs. rental use):                        TCJA interest deduction rules
                                                Generally, under the TCJA, interest paid or accrued by a business is deductible
Rental property. You can deduct rental
                                                only up to 30% of adjusted taxable income (ATI). Taxpayers with average annual
expenses, including losses, subject to
                                                gross receipts of $25 million or less for the three previous tax years generally
the real estate activity rules discussed
                                                are exempt from the limitation. Larger real property businesses can elect to con-
at right. Property tax attributable to
                                                tinue to fully deduct their interest, but then they’re required to use the alternative
the rental use of the home isn’t subject
                                                depreciation system for real property used in the business.
to the SALT limit. You can’t deduct
any interest that’s attributable to your        The CARES Act increases the interest expense deduction limit to 50% of ATI
personal use of the home. However,              for the 2019 and 2020 tax years. (Special partnership rules apply for 2019.) It
you can take the personal portion of            also permits businesses to elect to use 2019 ATI, rather than 2020 ATI, for the
property tax as an itemized deduction           2020 calculation, which may increase the amount of the deduction.
(subject to the SALT limit).
                                                If these changes reduce your tax liability for 2019, you may be able to file an
Nonrental property. You can deduct              amended return to receive a refund now.
rental expenses only to the extent of
your rental or other passive income.
Any excess can be carried forward to          Real estate activity rules                     for the following improvements to
offset rental income in future years. You     Income and losses from investment real         nonresidential real property: roofs,
also can take an itemized deduction for       estate or rental property are passive by       HVAC equipment, fire protection and
the personal portion of both mortgage         definition — unless you’re a real estate       alarm systems, and security systems.
interest and property taxes, subject to       professional. Why is this important?
the applicable limits. In some instances,     Passive activity income and losses have        For qualifying property placed in
it may be beneficial to reduce personal       some negative tax consequences. (See           service in 2020, the expensing limit
use of a residence so it will be classified   “Passive activities” on page 10.)              is $1.04 million. The break begins
as a rental property.                                                                        to phase out dollar-for-dollar when
                                              To qualify as a real estate professional,      asset acquisitions for the year exceed
Home sales                                    you must annually perform:                     $2.59 million. (These amounts are
When you sell your principal residence,                                                      adjusted annually for inflation.)
you can exclude up to $250,000 of gain        y	More than 50% of your personal
($500,000 for married couples filing             services in real property trades or         Other valuable breaks include bonus
jointly) if you meet certain tests. Gain         businesses in which you materially          depreciation and accelerated deprecia-
that qualifies for exclusion will also be        participate, and                            tion. (See “What’s new!” at left.)
excluded from the 3.8% NIIT. (See
                                              y	More than 750 hours of service in           Tax-deferral strategies
page 11.) To support an accurate tax
                                                 these businesses during the year.
basis, maintain thorough records, includ-                                                    It’s possible to divest yourself of appreci-
ing information on your original cost                                                        ated investment real estate but defer the
                                              Keep in mind that special rules for
and subsequent improvements, reduced                                                         tax liability. Such strategies may even
                                              spouses may help you meet the material
by any casualty losses and depreciation                                                      help you keep your income low enough
                                              participation test. Warning: To help
claimed based on business use. Warning:                                                      to avoid triggering the 3.8% NIIT and
                                              withstand IRS scrutiny, be sure to keep
Gain that’s allocable to a period of “non-                                                   the 20% long-term capital gains rate.
                                              adequate records of time spent.
qualified” use generally isn’t excludable.                                                   Consider these deferral strategies:

Losses on the sale of any personal            Depreciation-related breaks                    Installment sale. An installment sale
residence aren’t deductible. But if part      Valuable depreciation-related                  allows you to defer gains by spreading
of your home is rented out or used            breaks may be available to real                them over several years as you receive
exclusively for your business, the loss       estate investors. One such break is            the proceeds. Warning: Ordinary gain
attributable to that portion may be           the Sec. 179 expensing election. It            from certain depreciation recapture is
deductible.                                   allows you to deduct (rather than              recognized in the year of sale, even if
                                              depreciate over a number of years)             no cash is received.
Because a second home is ineligible for       qualified improvement property —
the gain exclusion, consider converting       a definition expanded by the TCJA              Sec. 1031 exchange. Also known as
it to rental use before selling. It can be    from leasehold-improvement, restau-            a “like-kind” exchange, this technique
considered a business asset, and you may      rant and retail-improvement property.          allows you to exchange one real estate
be able to defer tax on any gains through                                                    investment property for another and
an installment sale or a Section 1031         The TCJA also allows Sec. 179                  defer paying tax on any gain until
exchange. Or you may be able to deduct        expensing for certain depreciable              you sell the replacement property.
a loss, but only to the extent attributable   tangible personal property used pre-           Discuss the limits and risks with your
to a decline in value after the conversion.   dominantly to furnish lodging and              tax advisor.
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