Small Business Taxes & ManagementTM--Copyright 2016, A/N Group, Inc.
This is the final article in our series on tax planning. We recently posted our Year-End Planning--Part 2--Businesses article and an article Year-End Planning--Part 1--2016 Basics. Please make sure you've read these before continuing. For most business owners (S corporation shareholders, partners, and sole proprietors) this is where you put it all together.
Last year the big question was whether or not a number of expiring provisions would be extended. Thankfully, that's not a problem this year. In fact some of those expiring provisions have been made permanent. Now the question is what the tax law will look like in 2017. There appears to be no question at this point that tax rates will be lower. The standard deduction could be considerably higher, but itemized deductions such as the deduction for state and local taxes could be eliminated. And there could be an absolute cap on itemized deductions. But betting on other changes could be trickier. And there's also a question of timing. Major tax changes haven't come easy in the past. That could be different with one party in control of both houses and the presidency. Still, there's no guarantee all the changes will be effective in 2017. And paying for those changes could be an issue.
What's the takeaway? In most cases it'll make more sense than usual to defer income to next year and take deductions this year. Don't underestimate the importance of year-end planning. You can save big tax dollars by deferring or shifting income from one year to another. Next year is too late; even the end of December may be too late for some techniques.
Caution--Before taking any tax action, evaluate all the factors surrounding the decision. Don't risk an economic loss for a small tax saving. Even if you're in the highest bracket (figure federal and state), a $1 tax deduction won't save more than about 45 cents in taxes (about 48 cents if it's a business deduction and you're subject to the self-employment tax). That means a $100 expenditure will cost you $55 out of pocket; more if you're in a lower bracket. The best tax planning moves are those that don't cost you anything or increase your risk but merely save taxes such as moving deductions between years.
Planning Point--We won't talk much about the 0.9% Medicare tax on salaries above $200,000 ($250,000 married, joint) in AGI. There's not too much you can do about it, and the amount is relatively small--$900 on $100,000. That brings up a point. If you're a business owner with a relatively complex return, unless you plan to spend a couple of weekends on running numbers--or make your CPA rich--there are too many variables to maximize your tax savings. Start out by securing the biggest savings and then, if possible, tweak the finer points.
For tax rates and brackets, phaseouts, AMT rates, etc. go to 2016--Tax Facts for Individuals
2016 Tax Landscape
The top tax rate for 2016 is 39.6%, the same as last year. That makes tax planning more important than in earlier years. In addition, the next bracket down is 35%, but it's very narrow. For a married couple filing joint the 35% bracket extends from $413,350 to $466,950; that's only some $53,600 wide. The 39.6% bracket starts at $466,950. In contrast, the 33% bracket is $181,900 wide. For single individuals the situation is even worse. The 35% bracket is less than $1,700. It goes from $413,350 to $415,050. The 39.6% bracket starts at $415,050. For all practical purposes there is no 35% bracket for single individuals. That means you not only want to try and avoid the top bracket, you want to avoid the 35% bracket to leave some room for error.
The top rate for long-term capital gains is 20% (plus the net income tax, see below) and applies to taxpayers in the 39.6% bracket. That's another incentive to stay out of the 39.6% bracket and makes tax planning for single individuals very important. Taxpayers in the 10% or 15% bracket pay no tax on long-term capital gains; those in the 25%, 28%, 33%, and 35% brackets pay 15%.
The net investment income tax of 3.8% applies to net gain or loss from the disposition of property (capital gains plus other gains or losses from Form 4797, i.e. business gains and losses), interest income, dividends, annuities from nonqualified plans, rent and royalty income and income from passive activities, e.g., a partnership in which you do not materially participate. The tax applies if your adjusted gross income exceeds $200,000 ($250,000 for married filing joint; $125,000 for married filing separate). That's a fairly low threshold. Many business owners are likely to be caught in the net. The net result is a capital gains rate of 18.8% (not 15%) or 23.8% (not 20%) with interest income, short-term gains, etc. taxed as much 43.4% (39.6% + 3.8%).
The phaseouts of itemized deductions and exemptions. Phaseouts begin at AGI of $259,400 for single individuals and $311,300 for married couples filing joint. On $100,000 of AGI over the threshold you'll lose $3,000 of deductions. Other items such as personal exemptions, AMT exemption, etc. are also subject to phaseout.
Lastly, there's an additional Medicare tax of 0.9% on wages and self-employment income in excess of $200,000 ($250,000 for married joint; $125,000 for those filing married separate). There may not be much you can do to avoid this tax and, fortunately, it's fairly minor ($900 on $100,000 of income). S corporation shareholders may be able to reduce their salary, but you still must take a reasonable amount. Partners and sole proprietors may be able to shift income to avoid the threshold if you'd normally wouldn't come close to it, but break it one year. Because of the amount is likely to be small, so would any savings.
Finally, the tax brackets for trusts are particularly narrow. First, there is no 10% bracket; the lowest tax rate is 15%. Second, there is no 35% bracket. Third, any income over $12,400 is taxed at 39.6%. That makes leaving undistributed income in a trust particularly expensive. This is an area to discuss with your tax advisor.
Based on the tax proposals released, taxpayers in the highest brackets will benefit the most from the rate reductions. The question is by how much and at what thresholds.
Tax rate differences. This is a basic tax-planning strategy. If you're in a high bracket this year but expect to be in a lower one in 2017, you want to defer income to next year (or accelerate deductions to this year). While it's less likely than in prior years, you could overdo it and end up pushing yourself into a higher bracket next year. It's possible if you're at the lower end of the income range and defer a large amount to 2017. In the unlikely situation you expect to be in a higher bracket next year, you may want to accelerate income into 2016 and delay deductions. Again, don't overdo it.
Another point. Many benefits are phased out for taxpayers above certain AGI thresholds. For example, if both you and your spouse are covered by a pension plan, deductible contributions to an IRA are phased out if your modified AGI exceeds $98,000. Because there are a number of these phaseouts, and they occur at various AGI amounts, you can't plan for all of them. However, you should be especially careful if your AGI is near $100,000. And one phaseout can be critical. For married taxpayers filing jointly, the American Opportunity Credit is phased out for AGI levels over $160,000 ($80,000 for single taxpayers). If you have two children in college and they would both qualify for the credit of $2,500 each, you could lose $5,000. And that's a tax credit, not simply a deduction. You may want to defer income from this year into next, (or accelerate income into this year if they'll be starting school next year) to maximize use of the credit.
Example--For 2016 you're in the 15% bracket. Because you expect to close a big deal in 2017 you anticipate being in the 25% bracket, but you project falling back to the 15% bracket in 2018. Accelerating some income into 2016 might make sense.Making such a shift is now more important than ever. If you can switch income out of the 39.6% bracket this year into, say the 33% bracket you save 6.6 percentage points on the income. In addition, you'll save 5 percentage points on the capital gains since the rate will drop from 20% to 15%. That's particularly important in a year where you have large long-term capital gains.
Deferring income. How do you defer income? (The discussion here doesn't include business income on a Schedule C. See our Year-End Planning--Part 2--Businesses.) There aren't too many options on your individual return, especially this late in the year. And keep in mind that you can't avoid income by simply not cashing the check, even if you're on the cash method of accounting.
In the case of a regular corporation, the corporation will lose the deduction if you have more than a 50% interest in the business. The amount will only be deductible when paid.
Caution. If your business lost money in 2016 or a prior year or you expect a big loss in 2017, you may have a net operating loss (NOL) which you may be able to carry back to an earlier year. There are a number of options, making rules of thumb tough. See Year-End Planning--Part 2--Businesses for more information and talk to your tax adviser.Accelerating deductions. In addition to deferring income, one way to lower your taxable income in 2016 is to accelerate deductions. Here are some options.
If you make charitable donations of property of more than $500 you'll have to file a special form with your return. Donations of household goods or clothing that are not in good used condition or better are allowed only if the deduction for a single item exceeds $500 and a qualified appraisal is attached to the return. (The appraisal requirement makes such donations unattractive.) Special rules apply to vehicle donations of over $500. Donate more than $5,000 of similar property and you'll need a formal appraisal. (E.g., $3,000 of artwork to the Madison Public Library and $2,500 of paintings to the Chatham Museum.) Publicly held stock for which market quotations are available escape this requirement. An appraisal summary has to be partially completed for nonpublicly traded stock valued at $5,000 to $10,000. A full appraisal is needed for nonpublicly traded stock if the contribution exceeds $10,000. You might want to avoid those thresholds.
While charitable contributions should be retained under any new legislation, there are no guarantees here. While there are limitations on contributions based on your AGI, most taxpayers won't come close.
You might investigate a charitable lead or unitrust. You can deduct much more, but this is not a planning move to be taken lightly. Get good advice. Another option is a "donor advised fund". You can contribute a large amount this year, and decide on who gets the money down the road. You do this by making the contribution to a mutual fund or similar financial institution that allows such plans. Most institutions set a minimum contribution of $10,000.
If you have to take a required minimum distribution from your IRA, consider making distribution (or part of it) directly to a charity. That'll keep your AGI down because it'll never count as income. That's a big benefit because the lower AGI may allow you to avoid the AMT, the net investment income tax, etc. There's a $100,000 limit per year.
Caution--Some items are not deductible for alternative minimum tax (AMT) purposes. They include taxes, interest on a home mortgage other than a mortgage to purchase or improve your principal residence and one other home that is a qualified dwelling, and miscellaneous itemized deductions. In addition, only medical expenses that exceed 10% of your AGI are deductible. So taking big deductions for taxes could trigger an alternative minimum tax problem. See below for a more detailed discussion of the AMT.
How to pay. If you're a cash-basis taxpayer (almost all individuals are), you can deduct payments made by December 31. There's no problem with cash (get a receipt). Checks must be in the mail by December 31. Do it a few days earlier to avoid having to prove the mailing date. Credit card payments are considered made when you sign the authorization slip, even if you don't pay off the card for some time. IOUs or notes don't count until they're actually paid.
Accelerate income--defer deductions. What if you think you'll be in a higher bracket next year? For example, you know you'll be closing on a big deal, or you're selling a business and you'll have a lot of ordinary income on the sale. Another twist involves the alternative minimum tax (AMT). If you're going to be hit with it no matter what you do, accelerate income into 2016. The AMT tax rates are 26% and 28%. This requires careful planning; too much income and you'll be paying the higher regular tax. Some techniques are just the reverse of what we've discussed above. Here are some other thoughts.
NOTE. Accelerating income into 2016 is decidedly risky unless you know you're going to be in a substantially higher bracket next year. And no one is really sure where the rates will break. One such scenario could be your business did little better than breakeven this year and your spouse was unemployed for most of the year. Or you had extraordinary medical expenses. And you're sure your income will easily break $100,000 next year. Talk to your tax advisor about your situation.
How do you collect on the installment notes? The most straightforward way is to ask the buyer to pay the balance of the note (or a part of the balance) before the end of the year. If that doesn't work, you might be able to sell the note to a third party. Unless the interest rate is attractive, you may have to take a discount. Factor that into your analysis. Finally, if you pledge the note as collateral for a loan, the note will be deemed to be paid.
Delaying deductions may be fairly easy to do. Just don't pay the bills. If real estate taxes are due late in the year you might delay payment to next year. That last installment of estimated state taxes can be paid in early 2016. Take into account any late payment penalty. It's best not to delay paying your home mortgage. You don't want to hurt your credit rating. Charitable contributions can be put off till next year.
You might also delay some medical expenses such as a routine physical, payment of medical insurance, etc. However, if you might make the 10% (7.5%) threshold this year, but not next, it makes sense to take the deduction this year. A deduction at 15% is still worth more than no deduction at all.
Before taking action also consider any potential changes in your life that could affect your taxes. A divorce, marriage, or death can significantly affect your tax bracket. So can the loss of exemptions, e.g., children leaving the nest--or a new addition. Retirement, loss of a job, an inheritance (IRAs, pensions, etc. left to you can be taxable) all can affect your bracket and taxes. Same-sex couples who get married in a state that recognizes such marriages have to file as married, or married filing separate. That's true even if they live in a state that doesn't recognize such unions. The list of states recognizing same-sex marriage has grown significantly.
Generating cash. If you need cash for your business, a new home, college tuition, etc. planning ahead can save you taxes. Some of the techniques above will generate cash, but at a price.
If you're thinking about any of the above strategies, you need to talk to your tax and financial advisors. The tax rules can be tricky and the consequences substantial.
Alternative minimum tax. The idea behind this tax (AMT) is to make sure even taxpayers with big deductions pay at least a minimum amount of tax. At least that was the theory when the law was written in 1969. The tax rate is 26% on the first $186,300 (2016; indexed for inflation) of alternative minimum taxable income (AMTI), and 28% on amounts above that level. While the rate sounds attractive, your AMTI is sure to be higher than your regular taxable income. That's because you can't deduct taxes, some home mortgage interest and miscellaneous itemized deductions. Your deduction for investment interest may be limited and your deduction for medical expenses is only the amount that exceeds 10% of your AGI. Income from certain municipal bonds that's tax-exempt for regular income tax purposes may be taxable for AMT purposes. Finally, the 26% and 28% rates apply to all your AMTI; for regular tax purposes you're only paying 10% on your initial income, no matter how much you earn.
In addition, you may have to increase your AMTI for excess depreciation from rental properties, S corporations, partnerships, or a Schedule C (sole proprietorship). Other adjustments include income from the exercise of incentive stock options, any difference between regular taxable income and AMTI from certain passive activities, and adjustments for depletion and intangible drilling costs. While there are some other adjustments, you're unlikely to encounter them. Some of these differences, such as depreciation, can turn around in later years, decreasing your AMTI.
Most of these adjustments will increase your AMTI. You're allowed an exemption ($83,800, married filing joint; $53,900 single in 2016) but it's phased out if your income exceeds $159,700 (married, joint) or $119,700 (single). Finally, if you pay the AMT as a result of a timing adjustment (e.g., depreciation), you may be entitled to a credit on next year's tax.
Because of the phase-out of the exemption, taxpayers with large capital gains will find that the capital gains may only be taxed at 15% but they'll be hit with the AMT despite relatively low ordinary income that wouldn't normally be subject to the AMT.
Sounds complicated? It is. It's pretty tough to plan for this tax without going carefully through the math or using a computer program. There's a lot of interaction. Here are some thoughts:
You can get some help at the IRS Web site at Alternative Minimum Tax Assistant for Individuals. The 2016 version has not yet been posted, but the 2015 version can give you a general idea how you'll be affected.
The is one of the best areas for tax planning. And, you've generally got till nearly the end of the year to act. There are plenty of good ideas in the discussion below. Just keep in mind that investment objectives should take precedence over tax saving motives.
Things changed materially in 2013 with respect to capital gains, and those rules continue to apply to 2016. First, the 3.8% tax on net investment income (NII) applies to taxpayers with AGI above $200,000 (single) or $250,000 (married, joint). That means for a married couple filing jointly above the threshold the capital gains rate is 18.8%, 25% more than in earlier years. For taxpayers in the 39.6% bracket, the rate on long-term gains is 20% plus the 3.8% tax on NII.
CAUTION. Keep in mind throughout this discussion, investment considerations are paramount.
Planning Point--Because the rates on long-term capital gains can vary from 0% to 23.8%, this is a critical area. Moreover, there are other traps. For example, losses can be carried forward; gains cannot. (There's an exception for assets sold on the installment method such as land, a rental property, etc. You can't sell marketable securities using the installment method.) Have $100,000 of gains and an equal amount of losses that you haven't realized? If you take the gain this year and the loss next year you'll pay tax on the gain but won't get an immediate benefit of the loss. (You can take $3,000 per year against ordinary income, or use it against 2017 gains.) Take the loss this year and the gain next and you can use the carryforward loss to offset the gain next year.Assess your positions. The first step is to find out where you stand. That is, list all your positions (stocks, bonds, and any other investments that you might consider selling). Include the date purchased, the purchase price, adjustments (reinvestment of dividends increase your basis, stock dividends and splits affect your basis, etc.), your adjusted cost basis, and the current market value. Then you can determine whether you have a gain or loss and how much. Here's a summary of the rates:
Planning Point--While long-term capital gains may be taxed at beneficial rates, those gains can affect many other areas of your tax liability. No matter how they're taxed, those gains will increase your adjusted gross income (AGI) and many thresholds are based on your AGI. Have losses on rental property? If your AGI is under $100,000, you can take up to $25,000 of net losses. The $25,000 exemption is phased out so when your AGI reaches $150,000, none of the losses are currently deductible (they can be carried forward). Likewise, as your AGI increases your AMT exemption is phased out. Your AGI affects a host of tax deductions and credits--education credits, IRA eligibility, medical and miscellaneous itemized deductions, dependent care credit, etc. It's a difficult balancing act.
Note. If you sold property on an installment basis, the tax rate is based on when the money is received, not when the sale was made. That is, you'll get the benefit of the current rates on property you sold on the installment basis some years ago. Or suffer the higher rates if capital gain rates increase.
Check your mutual fund or brokerage statement carefully. Some gain may be taxed at 25% (the unrecaptured depreciation) if you invested in a REIT (real estate investment trust) or you or your S corporation or partnership sold real estate.
Within each rate group, gains and losses are netted to arrive at a net gain or loss. The following additional netting and ordering rules apply. Short-term capital losses (including short-term capital loss carryovers) are applied first to reduce short-term capital gains, if any, otherwise taxable at ordinary income rates. A net short-term loss is then applied to reduce any net long-term gains from the 28% group, then to reduce gain in the 25% group, and finally to reduce net gain from sales taxed at 20%, 15% or 0%.
For long-term gains and losses, a net loss from the 28% group (including long-term capital loss carryovers) is used first to reduce gain from the 25% group, then to reduce gain from the 20/15% group. A net loss from the 20/15% group is used first to reduce net gain from the 28% group, then to reduce gain from the 25% group. Any resulting net capital gain that's attributable to a particular rate group is taxed at that group's marginal tax rate.
Fortunately, you're likely to only have to worry about short-term gains and losses (ordinary income treatment) and long-term ones (20%, 15% and 0% rate categories), not those in the 28% and 25% group. That will make planning easier.
Careful timing of your capital gains could produce some permanent tax savings. For example, you've got some stock with potentially (you haven't sold it yet) $3,000 of long-term (15%) gains. You've already sold stock that generated $3,000 in short-term losses. You don't think you can generate any short-term profits to offset the loss. It might make sense to hold off on taking the long-term gain. You can use the $3,000 loss to offset ordinary income this year. Then take the long-term gain next year and pay taxes at only 15% (plus 3.8%, if applicable). In other words, you're taking a deduction at, say 35%, and paying taxes at 18.80%.
Unfortunately, the market may not cooperate. You don't want to risk holding onto a stock that could decline in price, just to save some tax dollars. On the other hand, if you're selling real estate, it may be easy to postpone the sale into the following year. If you sell or sold property using an installment sale, you may also have some options in recognizing the income. Minimizing your tax bite isn't as easy as before. You'll have to spend more time with the numbers. If the gains are substantial, consult your financial or tax advisor.
You may have very few gains. But no matter what you do, investment considerations should come first. No tax deduction or gain reduction technique will offset a poor investment decision. And keep in mind that capital losses can be carried forward indefinitely, you can always use them against gains next year. Capital gains taken and not used to offset losses can't be carried forward; they're taxable immediately.
You want to try and avoid taking net gains in a year when you're subject to the NII tax or, worse, you're in the 39.6% bracket. There's not much you can do if you regularly earn $600,000 a year, but you may be able to secure a lower rate on capital gains if, say you're income fluctuates between $180,000 and $300,000 by timing the gains.
You should be especially cautious if your taxable income puts you in the 35% or low 39.6% bracket. That's because the 35% bracket is so narrow.
Even if you can't play the rate game described above, some approaches still work:
Sell capital gain property. If you've already realized some losses during the year, you might want to take enough in capital gains to offset the losses. If unused, the losses can be carried forward indefinitely and used to offset gains or up to $3,000 in ordinary income in any one year. That may be small comfort if you've got a substantial loss carryforward. ($100,000 in losses at $3,000 a year will take over 33 years to use.) Analyze your positions to decide if you'll continue to have substantial gains in the future. If not, consider selling stock at a gain now to use the loss.
Generate losses to offset gains. If you've realized gains during the year, consider selling positions where you have a loss, but only after assessing the investment's potential. Don't forget that any mutual fund holdings (other than those in an IRA, Keogh, etc.) will probably generate some long-term capital gains through distributions before the end of the year.
Converting short-term into long-term gains. Gains on property held more than 12 months are taxed at no more than 23.8% now; stock or other investments held 12 months or less produce short-term gains taxed at ordinary income rates, up to 43.4% (39.6% plus 3.8%).
If you're near the critical 12-month mark, you might want to consider holding on for just a little longer to take advantage of the lower rates. You've got to balance that against the chance that the price could fall. Generally, the closer you are to the 12-month threshold, the more you should consider holding out. The extra return could be substantial. For a formula to see how much you can lose and still break even by waiting, use the formula Breakeven Holding Period for Long-Term Capital Gains on our Formulas page.
Selling different lots. If you purchased shares at different times you can specify (do it in writing) to your broker which lot to sell. If you don't, the IRS assumes a FIFO (first-in, first-out rule applies). Selling the right lots can save considerable tax dollars.
Example--You bought 100 shares of Madison in 1990 for $4,000 and 100 shares in 1995 for $21,000. Madison's now trading at $100 a share so 100 shares are worth $10,000. You want to sell only 100 shares. If you tell your broker to sell the 1995 shares you'll have an $11,000 loss. If you don't specify which lot to sell, the shares bought for $4,000 in 1990 are the ones assumed sold and you'll have a reportable gain of $6,000.
Caution--Mandatory basis reporting by your broker applies to stock acquired after 2010. If you don't specify what shares you're selling the broker will probably report the sales on a first-in, first-out basis. Check with your broker on the mechanics.In the example above you could sell half your investment, take a loss, and still have a position in Madison, should a move to higher ground seem possible. The same rules apply to determine the length of the holding period. Sell one lot and you might have a short-term gain (or loss); sell a lot you held longer and you could have a long-term gain (or loss).
Another point. Even if both positions showed a gain, selling the one with the higher cost basis could reduce your position with the minimum amount of tax liability and end up generating more after-tax cash. Of course, if you've got substantial losses with scant hope of using them in the near future, selling the low-cost basis shares may make more sense.
Caution--The rules are more complicated when it comes to mutual funds. There are several methods of computing cost basis. That topic is beyond the scope of this article. Mutual fund companies now provide cost basis information on year-end statements or will give you that information if requested by phone. But that's only one of your options. And it may not be the best one. Also, see the Caution above on basis reporting by your broker.
Getting on in years? If you're older or in poor health, you should discuss your options with your tax adviser. The gain built into low-cost-basis shares might escape tax entirely because your heirs will receive a stepped-up basis in the shares. For example, you purchased 100 shares of Madison Software Inc. in the 80's for $1,000--it's now worth $500,000. If you hold the stock on your death your heirs could sell it the next day for $500,000 and pay no capital gains tax. But there are other issues to consider when planning for transferring property on death. If, on the other hand, on your death you have a loss in the stock, it will go unutilized.
Take the loss, regardless. If there's no chance of a comeback for the investment, consider taking at least some of the loss, even if you have no offsetting gains. Up to $3,000 of losses can be used against ordinary income. Additional losses can be carried forward to use against future gains or up to $3,000 a year can offset ordinary income. On the other hand, gains are fully taxable in the year of sale.
Collect bad debts. You cannot take a bad debt deduction for nonbusiness bad debts unless the debt is totally worthless. We can't go into details here, but most debts held by individuals are considered nonbusiness. You must be able to show you tried to collect the debt, but were unable to. This could take some time. Don't wait till the last minute.
Worthless stock. You can't just claim the stock is worthless. You have to be able to prove it. Even if the stock isn't quoted and the company is in bankruptcy, the IRS will claim it could recover. Sell the stock through your broker. If you can't, sell it to a colleague (not a relative; and get documentation).
Installment sale. An installment sale can spread a gain over several years. That may keep you out of a higher tax bracket and/or allow you to defer the gain to years when you might be in a lower bracket. In addition, that capital gain may be useful in later years to offset any capital losses. All that's necessary is that at least one payment is received in the next tax year. Should tax rates drop or for any other reason you can use the gain at little tax cost in a future year, there are ways to recognize the gain immediately. Talk to your tax adviser. Keep in mind that in the past installment gains have been taxed at the rate in effect when the gain is recognized, not when the sale was made.
Three cautions. You can't use the installment method for publicly traded stock and you've got be careful if you're selling tangible property. In the latter situation, any depreciation recapture is fully taxable in the year of the sale. It can't be deferred. Finally, you can't use the installment method if you're a dealer in that property. For example, you can sell a machine tool used in your business on the installment basis. On the other hand, if you're a dealer that sells such tools, you can't use the installment method.Charitable contribution of appreciated stock. This is an old technique, but it's very effective. If you make a charitable contribution of stock (you've held more than 12 months) that's appreciated in value you get to deduct the full fair market value as a charitable contribution. That's better than selling the stock and contributing the cash since you avoid paying capital gains tax and you also avoid increasing your adjusted gross income by the amount of the gain. The latter is important since many exemptions (e.g., the $25,000 rental real estate exemption) and thresholds are based on your AGI. Caution. There are some special rules. The most important is that your deduction is limited to 30% of your AGI. Any excess can be carried forward, but only for 5 years. So don't overdo it. Consider a charitable lead or remainder trust for large amounts.
Bond swaps. The idea is to sell bonds where you've got an unrealized loss, take the money and invest in bonds or other securities with a higher yield. This approach generally only makes sense if you can use the loss to offset other gains. The tax savings can be added back to the proceeds of the bond sale to provide additional capital.
Wash sales. You may have a loss in a position and want to take the loss this year, but like the stock and want to hold on. If you sell the stock (or bond) and purchase the identical security within 30 days before or after, the loss will be disallowed. For example, you sell 100 shares of Madison Inc. at a loss on November 28, 2016. If you bought 100 shares of Madison Inc. within the 30-day window, say on November 10, 2016 or December 20, 2016, the loss would not be allowed for tax purposes. It's not lost. Your basis is adjusted and you get the benefit when the new stock is sold.
The easiest way out of this situation is to wait 31 days before repurchasing the same securities. The second approach is to buy stock of another company in the same industry that is expected to perform similarly. Later you can buy back into your original holding. And one emerging growth mutual fund is not the same as another emerging growth mutual fund. CAUTION. A S&P 500 Index fund run by Madison Investments is the same as a S&P 500 Index fund run by Chatham Fidelity. Index funds can be identical.
The wash sale rule only applies to losses. You can sell a security with a profit, take the gain, and repurchase it immediately. This makes sense if you've got losses and you like the securities on which you're showing gains. For example, you bought KiWi Networks at $5 a share and it's selling for $100 but you think it will go higher. You can sell some shares, take the gain to offset losses and repurchase the shares the next day. If you do a 1-for-1 offset you pay no taxes on the sale, but have a new, higher basis in the new shares of KiWi.
Selling short against the box. In the past this technique could be used to effectively sell the stock (you got the cash and locked in the gain), without paying the tax. Moreover, you could defer the tax virtually indefinitely. That won't work any more. You can use the approach to postpone a gain for 30 days into the following year. However, after you close the position you'll have to hold the stock for 60 days. That can expose you to substantial risk. Talk to your broker or financial adviser before considering this approach.
Passive activities. Do you own an interest in a partnership or S corporation that is a passive activity in your hands? The general rule is that passive losses can only be used to offset passive income, or deducted in full when the passive activity is disposed of completely.
You've got several options. The first is to do nothing. Any unused losses can be carried forward. But the losses are worth less and less each year because of the time value of money. On the plus side, if tax rates go up the losses will be worth more.
You might try selling the investment. But if you invested in a family business, be aware of the related party rules. Talk to your tax adviser.
Investment interest. As an individual, your interest deduction is generally limited to interest on a home mortgage, a home equity loan (but only up to $100,000 of principal), and investment interest. Investment interest is interest incurred to buy investment property--usually stocks, bonds, etc. (But not tax-exempt bonds. You can't deduct any interest associated with them.) The rule is that any investment interest is limited to your investment income for the year. Any excess can be carried forward. Investment income includes interest, nonqualifying dividends (dividends that don't qualify for the lower, capital gain tax rate), short-term gains, and, if a special election is made, long-term capital gains and qualifying dividends.
Example--You had $2,000 of margin interest during 2016. You had $1,200 of interest income from bank accounts and $200 of short-term gains. That's a total of $1,400 of investment income. You can deduct $1,400 of the margin interest. The unused $600 can be carried forward and deducted next year, if you have sufficient investment income.
It may be too late in the year to generate interest or dividend income, but you could create some net short-term capital gains by selling stock or bonds at a profit. Remember, investment considerations come first. Long-term capital gains and qualifying dividends can also be considered investment income, but only if you make an election to have them taxed at ordinary income rates. In some cases this election works, but you've got to run the numbers.
Investment interest doesn't have to come from a margin account, but you must be able to show the interest expense applies to the investments.
If you're a small business owner that operates through a regular corporation you may find yourself concerned about this trap if you borrowed money to purchase stock in the corporation, advanced equity capital, or loaned it additional funds.
Example--You borrowed $150,000 to purchase stock in Madison Inc. a regular corporation in which you have a 50% interest. You borrowed another $50,000 which you loaned to the corporation at 6%. During the year the corporation paid you $3,000 of interest on the loan. You paid interest of $18,000 on the $200,000 you borrowed. You have no other interest, dividend, or capital gain income. Since you only have $3,000 of investment income (the interest the corporation paid you) you can only deduct $3,000 of the interest. The remaining $15,000 can be carried forward.
Planning Point--In some cases you may be able to avail yourself of the 0% tax rate despite substantial income. First, you have to be married. Second, one spouse must have very little regular income. Third, you've got to file married, separate. The idea is the spouse with the lower income sells assets he or she owns or are transferred to him or her. Check with you advisor on the mechanics.Often the situation described in the example above won't reverse for several years. If the interest rate on the loan to the corporation were higher, you'd be able to deduct more of your investment interest. In some situations it might even make sense to pay a taxable dividend. There's no general rule here. Work through the numbers with your tax advisor.
S corporations, partnerships, LLCs etc. generally don't have this problem. Any such interest expense is deductible on Schedule E.
Here's a list of other tax saving strategies.
Deductible IRA rules. For 2016 you can make the maximum deductible IRA contribution ($5,500; plus $1,000 catchup if eligible) even if both you and your spouse are covered by pension plans if your AGI is $98,000 (phaseout over this amount) or less. Single individuals can deduct the maximum if their AGI is $61,000 or less.
Required minimum distribution. If you or your parents are required to take minimum distributions from their IRAs, etc. make sure you've made them before the end of the year. The penalty for not doing so is 50% of the amount that should have been withdrawn.
Convert a regular IRA to a Roth. But remember, the conversion will be taxable. Conversion makes sense if you're in a low bracket this year (e.g., your S corporation or partnership had a bad year) and expect to be in a higher bracket in retirement. For 2012 and later years there is no AGI limit.
Collected unemployment? In 2016 all the benefits are taxable.
Still single? If you get married by December 31, you're considered married for the whole year. You won't always save by getting married, and it's not much of a tax planning strategy, but if you were going to anyway, consider doing so before the end of the year. That advice applies to same-sex couples in states where the union is legal.
Education credits. The American Opportunity Tax Credit is still available. The credit applies to the first four years of a student's college education and is equal to 100% of the first $2,000 of qualified tuition and 25% of the next $2,000 for a maximum of $2,500. Phaseout begins at $80,000 for a single individual and $160,000 for a married couple filing joint. The credit can be claimed on tuition, fees, and course materials (e.g., books). The Lifetime Learning Credit may also be available. It's 20% of the first $10,000 of qualifying expenditures. Phaseout begins at $110,000 for those filing a joint return; $55,000 for all others.
Alternative energy credit. The credit caps for solar hot water, wind, and geothermal property have been eliminated. The credit is 30% and applies only to principal residence. The credits won't expire for a number of years, so you have time.
FSA (Flexible Spending Account). The end of the year may be your last chance to deplete your FSA. While some taxpayers will have another 2-1/2 months; that's only if your employer changed his rules. And remember, the rules have changed. You can't deduct nonprescription drugs, etc.
Same sex marriages. A marriage, whether between different or the same sex is now legal in all states. But same sex couples who marry must file as either married, joint, or married filing separate. There are substantial tax implications. And undoing the marriage requires a formal divorce.
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--Last Update 11/24/16