2 points to consider, (1) the lack of a really good domestic football league, and (2) not having appeared at a WC before.
If you consider Africa, the real influx of Africans into the bigger clubs really started after Cameroon made the splash in Italia 90. Then with consistent performances by African teams in successive WCs, Africa as a whole put itself on the football landscape.
De lack of consistent or successful WC appearances by English speaking Caribbean countries doesn't make noise for the region.
Also, if a scout has to take a look at a Trini, more than likely, he have to catch de man when Trini playing somebody, and how often do we play international games? And what if de man have an off-game on dat day? Where as if we had a quality league, he could catch a glimpse of de man on any given week, or even watch him during a practice session.
