IMO your on the right track, great time to "do-it"
Don't get hung up on "which boat" , do a little research on what has gone where and pick one that appeals to you.
Also don't go overboard (no pun intended!) on outfitting your new vessel with alot of "Stuff" and electronics you may find you won't use or need.
I would suggest you just assure the basic rig and get aboard, and as you begin your sailing adventure do a few short sails and spend some time aboard and you will quickly determine what you need to add or aquire and most likely what you need will be available w/out much searching, hence the initial intro sail(s) .
for example, buy boat on east coast USA. Sail coastal to Florida (or South if already in florida) towards Carib.(where you indicated you planned on going).
As you proceed south you will work out all/most basic boat issues and determine what you need for your own personal cruising style. Also, as you go you will meet others doing likewise and exchange experiences and ideas .
you'll find out quickly what your preferences are and if cruising is for you.
good luck, I did it this way and , it's definetely "for me"
Unfortunately , I decided to sail north last fall and allow myself to be "stuck" by the winter season and we miss being aboard and cruising, and are not enjoying the frozen north after 12-14 years ilower latitudes (oops).