Eric, I lived and flew out of St. Thomas in 1993-1994. I suspect that Fly-BVI is under different ownership now. The owner-pilot at the time was a very nice West Indian who let us jump seat anywhere.
I really enjoyed the British Virgin Islands (BVI) and the people there. I flew there probably 10 times per week. Crime there is very low, so low that the police do not carry firearms. The U.S. side is just the opposite, i.e. high crime.
The BVI's are spectacular, with great diving and all water sports. The weather is great all year around and only changes temperature a small amount seasonally.
Everyone that I worked with in St. Thomas would have preferred to move to the BVI's. I am not sure of the cost of housing there, but probably less expensive than St. Thomas.
Flying in general around the Virgin Islands and Puerto Rico is a lot of fun. It is rarely IMC and the view is always great.
Personally I really like Puerto Rico. San Juan is a big city with big city problems, but stay out of the problem areas, i.e. the projects. The largest mall in the Caribbean is located there (Mall of the Americas). I find Puerto Ricans to be very nice and helpful people.
Housing costs in Puerto Rico are much more reasonable and you have more choices there, i.e. homes, condos, etc. Learning some Spanish would go a long ways there, as Spanish is the first language and English is the second language. Anyone with a HS education should be able to speak English.
Island living is not for everyone, as far as the Virgin Islands, as they are very small. I frequently felt a little "island fever" there and flying off the island helped a lot. Puerto Rico is quite large so you don't get that feeling.
The only real negative with flying is having to clear customs at every landing. The USVI are outside the customs zone, so when you fly from there to Puerto Rico you have to clear customs. This of course goes for the BVI's, as they are a British Crown Colony. This is really a minor inconvenience. I found the customs folks to be very helpful. The immigration people in San Juan were jerks. We used to bring the customs/immigration folks at Beef Island pizzas from St. Thomas. They loved us!
Schooling is a big problem in the USVI, kind of like Hawaii. You must send your kids to Montessori or similar. I don't know anything about the schools in PR, but would presume that you would need to send any kids to private school unless they are fluent in Spanish.
Cheers,
