Employment?
I re-read the original query about employment.
Over the years I have known people who work seasonally north and south.
Specifically, marine mechanics, chefs, and golf pros. Those seasonal jobs won't get you any insurance, but you can work for years for the same employer at each end. Resorts often hire couples, and may provide limited housing. This is probably less common than it used to be, because, as you mention, people are looking for insurance and other benefits. I doubt you'll save much money this way for "real" retirement. It may work for awhile so you don't dig into your present savings and can still follow the sun.
I have a friend I ran into in Cody, WY. He sold a small business in NH, and his house and bought an RV. Both he and his wife were working in the same souvenir shop where I stumbled on them. Basically, they traveled and found employment for 6-7 months at a time as the tourist season shifted.
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