It's been probably 20 years ago now, since we've been in Florida now since 2006, that we seriously considered moving to the Caribbean. You are right, for Americans, it is a lot easier as far as paperwork to move to the USVI, and there is the thought that the USVI is technically part of the US. We never really seriously considered moving to SXM, as that time, it was extremely difficult for US citizens to get residency that allowed them to work and we knew that we would have to work, unless we hit the lottery! Ultimately we decided that it wasn't for us, for a bunch of reasons. I honestly don't think that I am cut out for island life, in terms of the STUFF that one has to put up with in order to live there. Hurricane season is the least of one's troubles. I don't deal well with stuff that doesn't work the way it's SUPPOSED to and if you can't do that, you don't have the constitution to survive, living in 'paradise'. The thing that cut it for us was medical care. When you get older and you need GOOD medical care, for SERIOUS things, island life can be challenging.

We compromised and moved to Florida. I don't regret it for a minute, in terms of the weather. (Now the MONEY sucks in Florida, but that's a whole different issue... )

As always, Pat's advice is wise. If you are considering taking the plunge, rent somewhere for a year and see how you cope with what's required.