your requirements... trailerable, blue water capable, and 30k. and oh, by the way, you want it to take you to the caribe as well.... hmmm, good luck, and as they say in texas... "bless your heart"
forget new. period. A used boat, (I'm going to refrain from brand names) will be the only way you'll get all of that in one package... now, I'm not solicting your business, but a Marine Surveyor is how...
"since I don't know what to look for in terms of potential problems with used boats."
now, perhaps a better tact might be to get a "learner" boat now, trailer it around all you want, then, when the time comes, sell her, and get yourself a boat to take to the land of rum.
We are not primarily on earth to see through one another, but to see one another through
Some people are like slinkies: not really good for anything... but you can't help laughing when you push them down the stairs