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When I retired, I was recruited to be a MSF Instructor........I passed.....Most of the work was on weekends, a long ways away and not much pay.......
Regarding paying for Medical Ins........I have many friends in that boat, cost can be anywhere from 12-30K per year for a couple........Not cheap at all........
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The MSF classes here are all weekend for the beginning course and until fully retired, that would not work. The driver training is more weekday based, 2 hour classes 3 days per week then driving with students. I know the pay won't match what I am making now but if I can work less, pay for my medical and have some fun it would be ok.
My wife is 61 and paying for her own medical given that she works in a very small dental office with 5 staff. She is currently over $600/month with a silver level plan. A couple of years ago it was in the $300's. I'm not trying to start an Obamacare thread so please don't send it there.