AB Trini, it is possible for the smaller islands. Islands like Jamaica, Haiti, and even Trinbago, won't buy into that because they believe that it is possible to make it to the world cup on their own.
I believe merging some of the islands to form a more competitive team was entertained before. For it to work it would make sense to put the islands that are closer and have more cultural ties together. Putting all the islands together will be a mess. I think 3 or 4 competitive teams can come out of merging some of the islands together.
Grenada and SVG
St Lucia and Dominica
SKN, Antigua and Barbuda and Montserrat
BVI, UVI Anguilla
Martinique and Guadeloupe (They will be a powerhouse)
Aruba and Bonaire (Curacao won't buy into joining. . All 3 used to compete as the Netherlands Antilles, they never had their Dutch players, if they reunited, they will also be a force)
Guyana and Suriname? Nope. They might be close in proximity. But culturally they are a bit different and it might not work.
Bahamas and Bermuda? Possibly.
Guyana and Barbados might work. But both will need to put their pride aside for this to happen. In fact all the nations will have to do that.