My wife and I are taking our "trial retirement" on St John, this summer. I have 2 quick questions.
1. Is a full size Escalade too big to be practical
2. Does the VI tax capital gains at a lower level, similar to mainland
I don't live on St John, but my personal experience is that it would be too big. It certainly would work, but the poor turning radius would annoy me dealing with all the switchbacks. I have a 4D Wrangler, but when on STJ I rent 2D Wranglers because they're easier to maneuver and park in tight spaces.
Disclaimer: I'm from St Croix 🙂
I drive a Ford Excursions here on STX. No issues, it makes a great touring car for guests and restaurant runs when several are going.
Before I brought from California it there were several on this page that tried to discourage me.
My advise is to do what you want, that's why we moved here!
Regarding taxes, I do my own, they are identical to the 1040 you file in the states except you must be here at least half the tax year, pay quarterlies to the BIR and file with the BIR.
Be sure that you change your address with the IRS when you file with them the last time.
More complicated issues are best dealt with by an accountant.