U.S. TerritoriesPuerto Rico, Guam, U.S. Virgin Islands, etc.
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Bunch and efrenb5, many, many thanks to you both for your candid, honest, and very straightforward answers, and to gemstone for suggesting a very long visit/short term move. My spouse and I moved to the USVI (St. Croix) in 2005...we thought our 10 day pre-move visit was quite long enough (even though we were robbed at gunpoint - just a fluke, ya know?). The reality of actually living daily life on an island was so different than what we expected. We moved with job in hand (spouse is a pharmacist), which was about the only smart thing I can come up with off the top of my head that we did.
Byrsch, most definitely rent for whatever time you are there until you are positive this is the culmination of your dream...I would not tie myself into a long-term lease. Do NOT move all your worldly possessions - rent something that is furnished, rent furniture - but please don't take on that expense and then find your lovely items aren't fond of the sea air (I still have drawers that will forever remain in the closed position!).
I miss the weather every day - I miss the view every day - I do not miss the higher cost of everything, the endless bureaucracy, and some feeling of being resented. I am only speaking from an experience 5 years ago and on another island, but I wouldn't imagine there's a whole lotta difference. As far as speaking Spanish - by all means, dig in there and do it. The Crucians spoke English mixed with some dialect we could never hear (we're from the south, and islanders don't have long, drawn out vowels :-) We visited PR many times and I found the people to be wonderfully friendly and informative, but San Juan was an assault on the senses every time (no offense to those from SJ, it's just BUSY and loud!)
Enjoy - rent, consider yourself residents, and in a year revisit the whole idea again. I do hope this works out for you. There may be times you want to throw in the towel....we did after about 18-20 months because of the expense of things. I can now see we went about some things completely backwards; all that being said, we'd still be home in Arkansas again. Funny the things you miss....