From what I recall, mainland Europe has a more relaxed immigration policy than UK. For instance, Arsenal use a Belgium club to place players from Belgian colonies in Africa such as Congo. Once the player joins the Belgian club at 16, by the time he's 18 he can get a Belgian passport, and is therefore a EU citizen and can move on to Arsenal. Those who don't make the grade are sold or released.
Some research may be needed to confirm this, but I believe Spain recognise T&T as a former colony. If this is so, English clubs could place T&T players in Spain and after 2 years bring them to UK.
I have looked into this, but there are some problems. The major one is with the players who want to stay in college football until 18/19 and are then too old. The second is that there appears not to be enough talent in T&T for UK clubs to invest in this (they would be paying all the costs to the Spanish club).
Glen Hoddle has a nice academy in Spain with Graham Rix, and Spurs would be a natural fit, but they can invest their money in other countries where there are more numerous talented youngsters. However, if we can get 4 or 5 players out, then European clubs may change their minds.