Work permits are likely to be the biggest problem.
I will take the word of others on salary - the cost of living in the Caribbean is very hight for even what one would describe as a modest stsndard of living.
There are commercial pilots hrre in Barbados waiting for chances to fly and are pumping gas to feed themselves.
Mustique Air, SVG and others fly Senecas, Aero Commanders, Islandrs and the like - also small twin turbines - I also suggest the RSS (Regional Security System) and a newcomer in Barbados called Caricom Airways.
Overall though I would think there is very little chance without a family tie to the Caribbean or a very influential personal contact; in any case just writing letters/emails are unlikley to produce results.
Good luck though.