I recommend having a look at a web site that is a broker for insurance for global ( primarily non-USA based) nomads. Http://brokerfish.com
No affiliation at all. Many choices.
Need to understand in USA how the insurance pre approval process works too. Not as simple as seeing any doc anywhere.
W2R- this global lifestyle is not for everyone- definitely trade offs required and there are pluses and minuses. Lots of work to get sorted with some insurance. I won't debate that lifestyle aspect here but will say that we are in mid-upper 40s and DW and I are about to FIRE and look forward to some more adventures abroad while still young enough to enjoy fully. Balanced with being near and available for aging parents.
We may evaluate after 1-3 years whether or not to launch an encore career too... Depends how the investment returns and retirement budget works out. Irrespective of that I am fearful of getting bored so some form of paid work or a small business venture is a likely activity for us.
Take care !!