thanks for the replies and I am asking the questions in part to get myself out of the doldrums of work and not cruising
planning the trip is at least half of the fun and I have appreciated and had recieved a lot of great info before we left for the Bahamas last year...
we are moving to the greater annapolis area from nyc this spring so I will very much be looking forward to doing boat projects when I am not floating around the gulf of mexico while at work. I will be doing most of the pre cruise work myself/with friends, but the Trinidad suggestion is a great one (although I am not sure if my dodger can make it that far though haha). the only hired anything I plan on at this point is to have my rigging
checked out by a pro. It should be in good shape, but I would rather pay the "insurance" to have that checked out than not.