Yes it be difficult. On any Caribbean island, you need a work permit for a start.On any Caribean island there are local operators, they will make life difficult for you if you start hiring out your plane and stealing there business. I give you this advice based on working down there in 2003/04, flying aztec's /402/ Senecas. I worked for a co with a AOC, that's the only way.Save your $$$$$$