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Going back to OP's situation, I don't know that I'd rely too much on this since OP doesn't have any insurance established for the Schedule C business. (OP is covered by his wife's employer-sponsored insurance.) We all know I'm more conservative than you on these things, but what are your thoughts about that specific issue?

That really cuts to the crux of the issue if you ask me. (And I think you did!)

To be deductible as self-employed health insurance, you have to establish the insurance as a part of the overall plan for your business. I can certainly see that it is possible to use medicare as part of your insurance plan - it's just so much more cost-effective than a private plan for primary care. And you can always supplement it with additional insurance if you want more coverage.

I'd hesitate to take medicare as SE health insurance if someone over 65 just started a bit of SE work to keep busy during retirement. On the other hand, someone who has been self-employed for years and just happens to cross that magic 65 age and start on medicare I think would have a better argument for calling that SE health insurance. Particularly if they had been paying for health insurance all along and are just switching from a private plan to medicare.

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