How to maximize tax deductions with s-corp medical healthcare expenses?

[adm]

I had s-corp business this year (first year).

1. I was employed by big company for the first 3 month and had a health insurance subsidized through work for the first 3 months of the year January - March. My spouse was on COBRA at that time (it was cheaper that way)
2. I only had  S-corp income for the rest of the year ( 9 month  April - Dec) and had a not subsidized COBRA (full pay,) starting in April for the rest of the year.
3. My spouse unemployed whole year and  had  COBRA from different employer (full pay, not subsidized) for the first eight month of the year and when expired went to marketplace insurance (Sept - Dec)

Assuming that not subsidized COBRA is the grey zone, can I put all premiums for my spouse for the whole year (COBRA + marketplace insurance whole 12 months) and my COBRA part (April – December) as part of gross wages for my W2 Box 1 and 14 (and maybe 16)  and consequently to Form 1040, Schedule 1, Line 17?
If the first 3 months of my spouse premium  are not qualified for this should I put these three month to itemized deductions? Any other outlets for the most efficient tax healthcare deductions in my case?

[AmeliesUncle]

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@adm wrote:

Assuming that not subsidized COBRA is the grey zone,

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As you said, that is a big gray area.  While I would probably take it, I think most tax professionals would NOT take it.

Has the corporation been paying for it, either directly or by reimbursing you in the proper time frame of an Accountable Plan?  If not, it doesn't go on the W-2 nor does it qualify for the self-employed health insurance deduction.