Ok clearly your touching one aspect of the situation. Name one decent airline in the Caribbean region. The caribbean is a large region and if you put it together things aren't that great for the islanders on a whole. If you want to individualize it's even worse because as a pilot in the caribbean region you're flying old aircraft for peanuts. If your lucky enough to get on a nice aircraft it's still peanuts.
Living in a a shoe box like some said here in the forum isn't any different than still living with your parents which happens a lot in the Caribbean region. If you're worried about the cost of living that's everywhere some places better than others. Average salary of $2000 in the caribbean barely gets you anything descent to live in. If you're at LIAT you get paid in EC which is even worse than the dollar.
If you're lucky enough to be from the U.S. Virgin Islands you might stand a chance with a regional in the US hopefully you get on to a major or legacy if not they have the chance to bail with descent jet time and get a job else where because everywhere hires US pilots yet they don't hire expats for no positions. So after all that explain what's the difference now between living in that shoe box having the opportunity to fly something descent and flying a crap making peanuts living in your parents house? Hong Kong doesn't sound so bad. The caribbean is pretty but living wise you're in for a bumpy ride. The difference is opportunity which isn't blooming in the Caribbean region at the moment.