Good thread, i myself have been wondering the same...
I remember from way back since I used to play Eddie Hart youth football, every had some special dribblers.. Cornell Glenn and Kwame Wiltshire were some of the best "tun up men" in the league back then and they were always encouraged to take on players.
Trinidad football on the whole, our ability to "beats" used to be our biggest strength and at the same time our biggest weakness, nevertheless that natural ability is what separated us from our immediate counterparts in the region. Now that we don't even have that, we looking just like (if not worse) than everybody else.
I think there might be a few factors..
Less street ball being played means less natural dribbling ability being developed.
Also, with the increased exposure to modern footballing methods and systems over the years, "beatsing" is frowned on and being coached out of young players from an early age in favor of learning the game correctly. This is not something unique to T&T, I read an article recently where the academies in England were trying to re-introduce street football to allow youths to develop natural talent before getting into formal coaching setups.
And of course, too much other stuff for youths to do than run down a sweat every evening like long time.