One of the major things we should watch for is a Miami to Cuba submarine cable. The Miami area (and the Terremark/Verizon "NAP of the Americas" IX point/datacenter) is already the landing station for a ton of submarine cables going to latin america.

At present there are challenges at OSI layer 1 getting data into/out of Cuba, not including any government regulation/interference, just due to the lack of pipes. There's a fiber cable to Venezuela, but VZ is not very well connected internationally and there's significant challenges with any US company trying to acquire a circuit on that path (do you want to build a POP in Caracas, with what's going on there right now?)