As I noted above, I was hanging my hat on a bit of ambiguity in the 535 language: " I looked at IRS Publication 535 which covers this but it left me confused. It is clear that to deduct health insurance premiums the plan must be "established under the business." We don't qualify. But after that it address Medicare Part B premiums and Long Term Care premiums. To me these appear to be separate matters but the language is confusing. What ever happened to the government efforts to use plain language? "
I think your reading that the "established" requirement applies to basic health insurance, Medicare premiums, and LTC premiums makes more sense than my wishful thinking. I was testing Free Tax online to see how it compared to TT in ease of use and thoroughness and went back to see why I had not entered the LTC benefits when I first ran through it. I noticed that when it got to the question regarding insurance it asked something along the lines of "Did you pay the premiums for health insurance or long term care insurance under a plan established y the business?" That language led me to pass on by.