As your question is about eligibility, (can he TAKE the deduction) I thought of a couple of things that MIGHT affect, or limit, that:
(1) Eligibility is determined month-by-month
He can only claim the health insurance premiums write-off for months when neither he nor his spouse (if any) were eligible to participate in any employer-subsidized (group) health plan.
For example, lets say he's single and left his employer to BE an independent contractor in June, then he can only deduct the premiums he paid for the last six months of the year.
(2) There's an earned income limitation
The deduction can't be more than the profit he makes from his business.
For example, if his self-employment
is a sole proprietorship, and he had a tax loss for the year, then he's not allowed to claim the deduction because his contractor didn't generate any positive earned income.
Sorry for the data-dump, but again, since your question was whether or he could take the deduction, I wanted to cover all the bases and list the two things that might still get in the way.
Let me know if you have ANY questions at all...
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