Retirees whatcha living on?..........

HSA can be used for Medicare and Cobra premiums.
It's a little more complex I think. As I understand it eligibility and penalties are different before you turn 65 and are eligible for Medicare than after. Paying premiums before or after 65 with an HSA isn't illegal per se as I understand it, but there is a penalty and taxes will be due before 65..double whammy. I think after 65 the penalty goes away but taxes may still be due.
 
Retiring in 5 years (4 yrs, 10mo, 15dys, but who's counting?). Wife and I will both have military and Federal Civilian pensions. That will be about $120-140K/yr combined. Add in whatever social security is. Plus a million in 401K. Should be about $15K/month without touching the 401K. Retirement income will be roughly 60% of working income.
Wife and I will both start drawing SS at 62 as we both have good pensions and will not depend on SS to get by. If I knew I was going to live to 95 I'd wait, but my luck is I go early.

Will have about 7 years left on the mortgage. Living in Arkansas with relatively low cost of living. Major expenses to be cut out are flying for fun and probably less international travel.
 
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