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Situation: Tax return for someone who died. They were self-employed with a net profit and with itemized deductions that are worth more than the standard deduction.

The insurance expenses are more than the business net profit.

Schedule A limits the deduction to "qualified medical expenses that exceed 10 percent of adjusted gross income (AGI) for the year." I do understand that health insurance premiums, including LTC insurance, are considered medical expense, and that LTC deductions have further limitations.

  1. Is it possible to maximize the health insurance deduction by claiming some amount on 1040 Line 29 and some on Schedule A?

  2. Must one be claimed before the other, such as claim on line 29 first, then claim what you can on Schedule A (or vice-versa)?

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Ok, after scrutinizing and rescrutinizing the 1040 and the Schedule A, I think this answer is this:

  1. Yes, you can claim on both 1040 line 29 and on Schedule A.

  2. You must claim on 1040 line 29 first, because the amount is part of the calculation for AGI, and AGI is the basis for determining how much you can claim on Schedule A.

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