A Philoshopical Question
Some thoughts from someone not yet there (so take it for what it''s worth):
Some advantages to getting a "real bluewater boat" in good shape might be the peace of mind that the boat would be better able to handle the stresses of severe weather, should you get caught in it. Also, if you choose to cross oceans, you already have a boat to handle it, rather than having to sell your coastal cruiser and start over.
Some possible disadvantages to buying a bluewater boat that you don''t ever really take offshore might be the extra expense of the purchase, and the fact that such a boat will likely be more work to sail and offer poorer light-air performance than a lighter purpose-designed coastal cruiser. [These are generalities and exceptions exist, I''m sure.]
Another comment I gleaned from other discussions is that sailing from the US down to and around the Caribbean is not necessarily "coastal" cruising. I guess if you are very good choosing weather windows, you could get by fine with just a plain vanilla coastal boat, but I''m told it''s not to be taken too lightly.
Good luck with your planning. Ok, the rest of you, now you can blast away. 8^)