Just out of curiosity what does your wife do for a living? If she makes decent money you should be able to support yourself and your family (From what I'm told). Also, it helps if the kids are in school. And I also don't know if flying in the Caribean would be ideal for a family. If I'm not mistaken the cost of living down there might be a bit high

Again, this is all from what I've heard from pilots both on this forum and in real life.