It looks as if way too many topics are being bantered here.
My approach would be that the insurance is NOT being offered by his "employer" (he is retired, correct?) and the premiums he is paying would qualify, with the usual dollar limitation restrictions, for the SEHI deduction.
Of course, "upon further review" of the original post - if the premiums being discussed are pre-tax (how the heck do you do that with retirement benefits???) then why are we even having this conversation in the first place?
As for the "plan being in the name of the business" issue - I thought that war had long ago been fought on these boards?
A self-employed Schedule C person is the business!FE
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