I was self-employed for 5 months in 2018 and received Obamacare during that time. I then got a job with employer health care. I earned enough in 2018 that I must now pay back the Obamacare subsidies through my taxes. So can I claim all premiums plus the subsidies that I received from Obamacare under self-employed health insurance?
Yes, that's what I would do. This is insurance that was paid by "you" ultimately for tax year 2018. And, since you are no longer self-employed, this is an expense that should have been counted in 2018.
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