Good thoughts, thanks for the input. Trying to summarize for the SEHID, also using 2012 Memo & Sec 162(l)(2)(B) as references. Still using the example that Sched C business is TP name only.

1) Would the SPOUSE post-tax 1099-R retirement plan health insurance be deductible as long as it's not "subsidized"? Or NOT deductible because it's NOT in TP name & it's NOT Medicare?

2) From 2012 Memo, Medicare premiums for TP/SP are ALL deductible as long as Sec 162(l) conditions are met

3) Sec 162(l) condition paraphrase = If TP is merely eligible for any Employer Subsidized coverage (through TP or SP), then can't deduct anything for SEHID. But retirement coverage is likely not subsidized, therefore OK to deduct Medicare.

So at this point, I think I can only deduct both Medicare premiums. Likely can NOT deduct the Spouse Retiree premium since the 2012 Memo was only about Medicare & the 7206 clearly states the policy must be in the name of the business or the individual. Does that make sense?

Yes, I'm probably overthinking it. But again, these numbers make a big difference.