Re: Long Term Live Aboard at St Tomas VI (US)
I can't help much with the local particulars, but have a few suggestions. First, if you're retired and sail, you have time on your hands. That's great. Drive to the nearest hub airport and direct flights to St. Thomas are going to be much cheaper. It seems its less than 4 hr drive to Atlanta from Bonifay. Rent a car one-way from Enterprise. Cheap.
While you may prefer the same slip year round, another consideration to alternate between a slip and at anchorage. That also allows one to move around between islands, even to the BVI, rather than be sedentary. However, you may be higher on a haul out list, if you're year round somewhere. That said, you might also be able to haul in a pinch in the BVI. Not sure. Easy ferry back and forth, anyway.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.