I lived down in Puerto Rico while I was based down there with Cape Air. Unfortunately with PR and the USVI you're still running into the good ol' USA economy. A lot of the companies that operate down there are mainland based. I hear good things about Seaborne though. I've talked to their pilots and they seem happy. Vieques Airlink guys seem pretty happy too. Nice thing about PR and the USVI is that they don't require anything more than your standard USA pilot certificates.
It was 10F with windchill here in PA this morning...missing PR everyday!