I Sell dish to PuertoRico, US Virgin Islands, and lots of yachts that go all over the carribean. Only issue is that the farther south and east you go, the weaker the signal from the sats. Down in PuertoRico, you need a much larger dish than Dish500.
Even so, Dish's caribean coverage is much better than DirecTV's since DirecTV does not even attempt to serve PuertoRico and USVI with their US Service.