Caribbean - Ron86 is correct - there was a thread on this and many of the nations there are just too poor to handle the travel costs. When you add up all the Caribbean nations, you have a decent population, but they are too numerous, too isolated geographically, too poor, and there are too many politically "troubled" nations like Cuba and Haiti that just aren't going to work well. Central America - this is an excellent idea (to combine some of their leagues), assuming that there are no political problems. US/Canada/Mexico - Triplet1 has the only solution: a conference-style setup. Because this is just too large a geographic area to cover. The only big problem that I see with merging Mexican clubs with US clubs into the same league is "middle American" cultural resistance. The "middle American" MLS fans (I'm thinking Kansas City and so on) are going to shoot that proposal down faster than you can say "no hablo espanol". The merger makes sense financially and every other way. But culturally it's too big a bridge to cross, at least any time soon.