Tax Planning Guide 2020 2021 - Year-round strategies to make the tax laws work for you
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2020 – 2021 Tax Planning Guide Year-round strategies to make the tax laws work for you 4783 E. Camp Lowell Drive • Tucson, AZ 85712 • P: 520-545-0500 • F: 520-545-0555
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
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,
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.)
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.
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.
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.
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
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.
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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