Considering moving from Florida looking for real advice

Which island? Have you done a PMV? That's the first recommendation. Long term rentals may be hard to come by right now due to Irma and Maria, especially on STT and STJ. Many rentals aren't widely advertised and are grabbed up by word of mouth or local sign out front. Vacation rentals for PMV should be coming available now with the high season over and FEMA starting to thin out, at least on STX. After reviewing all the previous discussions on this forum a PMV should help answer remaining questions. You can also meet up with a realtor during PMV that may be able to help with rentals later.

sorry if I sound lost but a PMV is ?

Pre Move Visit is PMV. We are all lost some of the time.

Long-term rentals are hard to find on STX as well. Housing is in short supply now as reflected in the Sunday Avis. Very few advertising since storms.

You will not find individual healthcare insurance unless you work for a company or the VI government that will provide it.