This is a very interesting observation, Truetrini. It's obvious that Cuba has some sort of coach school that prepares decent coaches. However, Cuban coaches tend to favor local players over foreign-based ones. For example, Haiti is going to face Chili on the 19th with a team that is even more "local" than the one you saw at the Caribbean cup. They do not like taking chances with players they do not know and they do not seem to be impressed with players from big foreign clubs. I believe that has to do with them growing up and learning their trade in a communist country where the focus is on the development of local resources as opposed to relying on foreign countries.
By the way, Armelio is sort of available and has been living in Miami since his Haiti adventure. He is returning to Haiti for the next season because he has just signed up with the Haitian club Victory but I am sure he would consider an offer from Trinidad. Armelio will replace Victory's current Ecuadorian coach. However, he will have a mammoth task to bring the moneyed but troubled club back to Haiti's top division.
One more thing about the apparent success of Cuban coaches in Haitian football is that these guys are pretty much at home in Haiti. Some Cubans assume they are of Haitian descent and that assumption is supported by the fact that these Cubans tend to speak fluent Haitian Creole, even those who have never been to Haiti (some Black ones are actually of Jamaican descent). There are large areas in Cuba where almost everybody can speak Creole. Armelio, for instance, is a creole-speaker. I guess being able to effectively communicate with your players from day one also helps.
To sum it up, would a good Cuban coach help Trinidad? I do not see why not. Just like Haiti, Trinidad has a plethora of local talents that Cuban coaches seemed to have been trained to mine and develop. It would certainly take them a couple more days to adapt, but they would eventually build a winning team out of the players they have available. Caution: THEY DO NOT LIKE WORKING WITH TOO MANY FOREIGN PLAYERS and I suspect many Trini fans have zero confidence in their local players.