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Dos and don'ts of tax deductions

The rules change yearly, but you have to learn them to play the game

Last updated: February 2013

Find the Deduction is a game with constantly shifting rules. Each year Congress changes something in the tax law, the Internal Revenue Service issues opinions, and tax courts make their rulings. If you like a challenge, learning this year's deduction options is like a game of chess. If you don't, it's a tedious round of hide-and-seek. But either way, it's worth knowing the rules, as outlined in our dos and don'ts below.

Charitable donations

Do pay attention to donation regulations. The IRS requires receipts for all deductible donations. All charitable deductions, no matter how small, must be substantiated either by a canceled check; bank record containing the charity’s name, donation amount, and date; or a detailed receipt from the charity. Otherwise the contribution is not deductible.

Do collect your charitable acknowledgements, receipts, and cancelled checks in one place. If you make cash donations, you'll need either a bank statement or a written communication from the charity noting the charity name, your donation amount, and the date. For more, check IRS Publication 526, "Charitable Contributions," [PDF] on the IRS website.

Don't claim donations of furniture, clothing, and other household goods that weren't in at least good condition when you gave them. While the IRS rule aims to weed out junk donations, taxpayers may claim a deduction of more than $500 for any single item in any condition as long as a qualified appraisal is included with their return.

Medical expenses

Do deduct premiums for the Medicare Part D prescription drug insurance program, as well as other health-insurance premiums you pay yourself. The premiums for long-term-care insurance are deductible on a sliding scale according to your age.

Do deduct gas mileage expenses for your car when used for medical reasons. The 2012 rate for such deductions was 23 cents per mile for medical travel.

Do read the IRS list of deductible medical and dental expenses in IRS Publication 502, "Medical and Dental Expenses." The following costs, for example, are deductible to the extent that they address a health issue: wigs recommended by a doctor for the mental health of a patient suffering hair loss due to disease, special mattresses and bed boards, back supports, elastic hosiery, childbirth classes, and remedial reading instruction for dyslexic children.

Don't expect much. You can only deduct unreimbursed medical and dental expenses that exceed 7.5 percent of your adjusted gross income. If you are subject to the alternative minimum tax, the floor is higher: 10 percent. But if you're self-employed, your health-insurance premiums may be 100 percent deductible. See Publication 502 for eligibility criteria.

Retirement accounts

Do contribute to an IRA if you're eligible. Taxpayers younger than 50 can put in up to $5,000 for 2012 and $5,500 for 2013; those 50 and older can sock away $6,000 for 2012 and $6,500 for 2013. For 2012, if you're single and covered by a retirement plan at work, your deduction for contributions to a traditional IRA will be phased out if your adjusted gross income is more than $58,000 but less than $68,000; the limits are $92,000 but less than $112,000 for joint filers. (After those upper limits, you get no deduction.) You have until the filing deadline to make a contribution. See IRS Publication 590, “Individual Retirement Arrangements,” for more information.

Do fund a SEP IRA if you made money from self-employment last year. You are eligible even if you held another job and contributed to a 401(k) there.