Medical equipment like wheelchairs, walkers, and other assistive devices are among the clearest examples of deductible medical expenses. The IRS allows a deduction for equipment that is medically necessary and prescribed by a doctor to diagnose, treat, or alleviate a physical condition. Crutches, hearing aids, blood pressure monitors, CPAP machines, and similar devices all qualify. As with other medical expenses, you need to itemize and the total must exceed 7.5 percent of your adjusted gross income before the deduction kicks in. Insurance reimbursements reduce the amount you can deduct, so only the portion you actually paid out of pocket counts.