Dictionary of Tax Deductions

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Edward A. Lyon, JD
TaxTuneup.com, Inc.
3416 Shaw Ave #5
Cincinnati OH 45208
513.321.2821

elyon@taxtuneup.com




Damages

Damages you win from a lawsuit or settlement are generally nontaxable, except for damages received to replace lost income:

  • Damages you receive for personal injury, including sickness, other bodily injuries, and other personal wrongs, are generally nontaxable.
     

  • Damages for libels and defamation against your business are taxable because those offenses damage your ability to earn taxable income.
     

  • Damages you receive under the Age Discrimination in Employment Act are taxable.
     

  • Damages you receive for emotional distress are generally taxable.
     

  • Damages you receive to compensate for the loss or destruction of property are nontaxable up to your adjusted Basis in the property.
     

  • Punitive damages are generally taxable, except for punitive damages arising out of injury or sickness.

Your attorney can give you more information regarding taxes on specific types of damages. In some cases, it may make sense to structure settlements, or even accept a smaller settlement, to allocate as much as possible to a nontaxable source.

Day Care

Day care costs for your dependent child or adult may qualify for the Dependent Care Credit. They may also qualify for pre-tax reimbursement through a dependent care Flexible Spending Account. These include costs for a day-care center, day camp, or nursery school. They also include an in-home babysitter, nanny, or au pair.

Day Trading

Day trading used to be America's favorite indoor sport. When tech stocks boomed, stock talk replaced baseball chatter around office coolers. And CNBC's daytime ratings regularly topped CNN's. All this is in spite of studies suggesting that 80% of day traders lost their shirts--even before the tech stock crash. You just didn't hear about them until they shot up their broker.

If you still have the fever, your deduction for day-trading expenses--commissions, software, online services, and the like--turn on whether you qualify as an "investor" or a "trader." If you're an investor, you deduct day-trading costs like any other Investment Expense, up to net investment income, subject to the 2% floor on Miscellaneous Itemized Deductions. But if you qualify as a trader, you can deduct 100% of your costs as a Business Expense on Schedule C.

Avoiding the 2% floor beats losing deductions. The trick is qualifying as a trader. To qualify, you'll need to meet three specific tests:

  • You trade full-time in lieu of a regular job. In other words, trading is your job.
     

  • You've established a regular and continuous pattern of trading nearly every day the market is open. You can certainly take vacations--in fact, you'll need them! But you can't trade in spurts.
     

  • Your intent is to profit from short-term market swings, not long-term gains or dividends. (You can maintain long-term stock investments. But you'll have to segregate them in a separate account to avoid disqualifying your trading activity.)

If you qualify, you can deduct 100% of your expenses, not just up to net investment income, and not just the portion that exceeds 2% of adjusted gross income. You can use First-Year Expensing to deduct capital equipment (Computers, etc.), rather than Depreciating them over time. And you can claim the Home Office Deduction.

You'll still report profits and losses as capital gains and losses on Schedule D. So you can't use day-trading gains as the basis for retirement plan contributions. But, on the bright side, you don't owe Self-Employment Tax on day-trading gains.

If all that sounds like a lot of effort to deduct just 2% of your income, you're right. If you generate $100,000 in net gains and you wind up in the 28% bracket, qualifying as a trader saves you just $560 in federal tax.

However, there's one last strategy for avoiding the 2% floor without the hyperactivity needed to qualify as a trader. You can form a separate legal entity, such as an S Corporation or Limited Liability Company, to hold your portfolio. The separate entity then deducts your day-trading costs as a business deduction, bypassing the 2% floor, and passes the income through to you. This strategy makes sense if your portfolio is large enough that the tax savings justify the cost of establishing and maintaining the separate entity.

Day trading isn't as easy as some of its promoters would have you believe. But disciplined day traders can make money--and lots of it. So the dream lives on, even when the market doesn't.

De Minimis Fringe Benefit

“De miminis” fringe benefits are property and services (not cash) that the IRS doesn’t tax because their value is “so small as to make accounting for it unreasonable or administratively impractical.” The generally accepted threshold for these items is $25.

If you operate your business as a Sole Proprietorship or Limited Liability Company, you're considered "self-employed," so you don't qualify for these employee benefits. (If you're married, you can hire your spouse and pay benefits through them. You don't need to pay your spouse any salary; however, you should be able to show that the benefits are 'reasonable compensation" for the services they provide.) If you operate as an S Corporation or C Corporation, you'll generally qualify yourself.

  • Occasional meals or “supper money” to let employees work "late" (10 or more hours in a day). The generally accepted threshold here is $20 twice weekly. Employees don't need to account for their use of the money.
     

  • Occasional cocktail parties, group meals, or picnics for employees and guests.
     

  • Traditional birthday or holiday gifts of property (not cash) with a low fair market value ($25 or less).
     

  • Occasional theatre or sporting event tickets.
     

  • Coffee, juice, and doughnuts you provide for employees at the office.
     

  • Flowers, fruits, books, or similar property you provide to employees under special occasions, such as illness, outstanding performance, or family crisis.

These may be mere rounding errors for the Microsofts of the world. But they can really add up! Most months have at least one holiday. And, while you can’t write off season tickets as a block, those trips to the ballet or local amusement park can add up.

Demolition

Costs you pay to destroy and remove an existing structure aren't deductible and don't qualify for Depreciation or First-Year Expensing. Instead, include them in the nondepreciable "land" portion of the property's Basis. 

Dentist

Deductible Medical Expense subject to the 7.5% floor.

Dentures

Deductible Medical Expense subject to the 7.5% floor.

Dependent Care Assistance

Dependent care assistance your employer provides to help defray day-care costs is nontaxable up to the lower of $6,000, your income, or your spouse's income. Payments you make to your own dependent child don't qualify for reimbursement under this break--you can't pay your 12-year-old to watch your infant.

Dependent Care Credit

The dependent care credit is a credit against your tax for day care expenses that let you (or both you and your spouse) work or look for work. This includes an in-home au-pair, babysitter, or nanny, as well as outside day-care costs. Here's how to claim the credit:

  • The credit is available for these "qualifying persons": a child under age 13, your incapacitated spouse, or any other incapacitated dependent.
     

  • If the incapacitated person has gross income of $3,500 or more, so that he or she doesn't qualify as a dependent, you can still claim the credit for the cost of his or her care.
     

  • Expenses outside the home include a day-care center, day camp, nursery school, or care in the home of a babysitter. Expenses inside the home include ordinary domestic services such as laundry, cleaning, and cooking plus Social Security, Medicare, and unemployment taxes on household employees.
     

  • Your day-care provider can't be your child, your spouse, or anyone else you can claim as a dependent. The credit is available for any dependent, including adults and parents as well as children.
     

  • Expenses that qualify for the dependent care credit may also be subject to the Nanny Tax.

The credit itself equals 20% to 30% of qualifying expenses up to a base of $3,000 (one dependent) or $6,000 (two or more dependents). If you're married and one spouse's income is below the base, the base is limited to the lower-paid spouse's income.

If your employer offers a dependent care flexible spending account, any reimbursements you claim from the account cuts your $3,000 or $6,000 base amount. If you have a choice, simply figure which strategy saves you more. Generally, as your tax bracket rises, the flexible spending account grows more valuable. The credit can also land you in Alternative Minimum Tax hot water by cutting your final tax bill below AMT levels.

Example 1: Your adjusted gross income is $25,000 and you're in the 15% bracket. If you put $4,800 into a dependent-care FSA, you'll save just $720, $336 less than the maximum $1,056 credit.

Example 2: Your adjusted gross income is $80,000 and you're in the 28% bracket. If you put the same $4,800 into a dependent-care FSA, you'll save $1,344, $384 more than the maximum credit.

Figure the credit on Form 2441 and carry the amount to Form 1040. For more information, see IRS Publication 503, "Child and Dependent Care Expenses."

Dependent (See Personal Exemptions)

Depreciation

Depreciation lets you write off the cost of a capital item (real estate, equipment, etc.) over a period intended to approximate the useful life of the property. A Computer, for example, qualifies as five-year property, which lets you write off one-fifth of the purchase price each year. The IRS publishes numerous depreciation schedules for various asset classes.

Many capital items qualify for "accelerated" depreciation, which lets you deduct a larger portion of the item's cost during the first years of ownership. The "modified accelerated cost recovery system," or MACRS, governs most accelerated depreciation schedules. A regular depreciation schedule for five year property might let you write off 10% in year one, 20% in years two through five, and 10% in year six, with the six-year period intended to keep you from writing off a full year's depreciation the year you buy the property. The MACRS 150% double-declining system, in contrast, lets you write off 20% in year one, 32% in year two, 19.2% in year three, 11.52% in years four and five, and 5.76% in year six.

Depreciation reduces a capital asset's Basis for figuring gain or loss on a later sale. If you sell an asset for more than that basis, you'll owe tax at ordinary rates on any "recapture" when you sell. (Real estate investors get a slight break; there's a special 25% rate for recapture of depreciated real estate.)

Example: You buy a truck for your business for $30,000. You depreciate $12,000 of the cost over the first two years, then sell the truck for $20,000. You'll owe tax at ordinary rates on the $2,000 "recaptured" in the sale.

You can depreciate any sort of capital equipment you buy for your business: computers and office equipment, cars and trucks, furniture. You can also use First-Year Expensing to deduct property immediately rather than depreciating it over time.

Cost Segregation is the process of allocating your investment in real estate among structural components such as walls, windows, and roofs (depreciable over 27.5 or 39 years) land improvements such as driveways, parking lots, and landscaping (depreciable over 15 years) and personal property such as carpets, cabinets, countertops, and appliances (depreciable over 5 years). Cost Segregation is one of the best-kept secrets in the Tax Code; be sure you understand how to use it to maximize deductions for your property.

Report depreciation and First-Year Expensing expenses on Form 4562, then carry the total to Schedule C, Form 1065, or your corporate return.

For more information, see IRS Publication 946, "How to Depreciate Property."

Dialysis

Deductible Medical Expense subject to the 7.5% floor.

Diaper Service

Deductible Medical Expense, subject to the 7.5% floor, for incontinence resulting from severe neurological disease (e.g., Alzheimer's).

Diets

Deductible Medical Expense, subject to the 7.5% floor, for diets prescribed for specific medical conditions, to the extent the prescribed diet costs more than a regular diet.

Disability Insurance

Disability premiums you pay for your own coverage are a nondeductible personal expense. If you own your own C Corporation, the corporation can deduct premiums for yourself and your employees.

Disability income insurance benefits you receive from a policy your employer pays for are taxable income. Benefits you receive from a policy you pay for personally are nontaxable income.

Dividends (See Life Insurance, Mutual Funds, and Qualified Corporate Dividends)

Dividends-Received Deduction

The dividends-received deduction lets a C Corporation (but not an S Corporation) exclude 70% of the dividend income it receives from another corporation (80% if it owns at least 20% of the paying corporation). The purpose is to avoid taxing the same income twice at the corporate level--ironic, considering the Tax Code eventually whacks the income again at the individual level.

Dividend Reinvestment Plans

Dividend reinvestment plans, or DRIPs, let you reinvest stock dividends paid in cash into additional shares. More than 1,000 publicly-traded companies offer these plans. Account fees are deductible as an Investment Expense, up to net investment income, subject to the 2% floor on Miscellaneous Itemized Deductions. And if the plan gives you a discount on new shares, the discount is taxable income the year you buy the shares.

DRIPs can be a cheap way to boost your holdings over time. But make sure plan fees and commissions don't overwhelm the benefits of buying in such small quantities. And recordkeeping can be a nightmare if you invest over time, then find yourself having to sell a block of shares with dozens of different cost bases.

Dogs of the Dow

The "dogs of the Dow" is a popular investment strategy based on the theory that high dividend yields indicate undervalued stocks. The mechanics are simple. Each year, rank the 30 stocks comprising the Dow Jones Industrial Average according to dividend yield. Buy equal dollar amounts of the 10 stocks with the highest yield. Hold the stocks for a year, and repeat the process annually. (There are several variations on this theme. Aggressive investors buy the five lowest-priced stocks from within the same group. The Motley Fool web site, at recommends a four-company variation called the "foolish four." And the newest version looks for the 10 Dow components with the highest "shareholder return," a figure that includes stock buybacks.) If you can't afford to buy individual stocks, you can buy mutual funds, unit investment trusts, and variable annuity subaccounts that use the dogs strategy.

Results appear impressive. From 1972 to 1989, the dogs returned an average of 19.03% per year, compared with 12.66% for the Dow Jones Industrial Index and 12.79% for the S&P 500. The dogs have beaten the Dow just 4 times in the 1990s, although I suspect this is due to the general underperformance by value stocks, and not any failure of the strategy. But, impressive as they are, do you see how these dogs practically sit up and beg the IRS to take your gains? First, the high dividends are taxed as ordinary income in the year you receive them. And second, the strategy forces you to realize capital gains each time a stock drops out of the high-yield group. You can hold your stocks for a year and a day to take advantage of lower rates on long-term capital gains. But you still whack your profits with each substitution. (There are generally two to five per year.) After taxes, the dogs lag a plain-vanilla S&P 500 index fund. The popular Dow 10 UITs sold by Merrill Lynch, Paine Webber, and other Wall Street firms are especially deadly because they sell all 10 stocks as each trust matures. This forces you to pay tax on all of your gains, not just those that drop out of the top 10 dividend yields. So kennel the dogs in your tax-deferred accounts.

For more information, see www.dogsofthedow.com.

Donor-Advised Funds

Donor-advised funds are an alternative to Charitable Trusts for donors who don't want the administrative headaches involved in setting up a trust. You give cash or securities to the fund--generally, $5,000 or more--and deduct the gift now. The fund manages your gift, and perhaps allows you to invest your principal among a group of "mutual fund" options. You can direct the fund to make gifts to your ultimate beneficiaries at any time.

Drug "Rehab"

Deductible Medical Expense, subject to the 7.5% floor (including meals and lodging during treatment). Even if you make eight trips to Betty Ford and still wind up in the can, like Robert Downey Jr.

Dry Cleaning (see Uniforms and Work Clothes and Travel)

Dues

Dues you pay to business, professional, and social groups may be deductible under these rules:

  • Dues you pay to professional organizations, chambers of commerce, and civic organizations (Kiwanis, etc.) are a deductible Business Expense on Schedule C, Form 1065, or your corporate return.
     

  • Dues you pay to charitable, religious, or educational organizations are a deductible Business Expense if you reasonably expect to gain some business benefit from your membership.
     

  • Dues you pay to those same organizations on behalf of your employer are a deductible Employee Business Expense subject to the 2% floor on Miscellaneous Itemized Deductions.
     

  • Union dues are a deductible Employee Business Expense subject to the 2% floor on Miscellaneous Itemized Deductions.
     

  • Personal dues you pay to charitable, religious, or educational organizations are a deductible Charitable Gift.
     

  • Health club dues are a deductible Medical Expense, subject to the 7.5% floor, if prescribed for a specific medical condition.
     

  • There's no deduction for private club dues such as lunch clubs and country clubs. However, you can deduct Meals and Entertainment you pay for at the club so long as the occasion qualifies for the deduction.

You can't deduct any part of union or professional group dues used for lobbying or political contributions. The organization should be able to furnish the amount of your dues used for this purpose.