Can I deduct my Medicare Part-B and Advantage Plan premiums for me and my wife as a sole proprietor of a side gig in retirement, ?

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Yes. In order to take the deduction your "side gig" will have to have a profit. Your deduction is limited to smaller of your health insurance or your business' profit. You cannot deduct your Medicare payments as self-employed health insurance and also as an itemized deduction for medical expenses on Schedule A.

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