My profile shows a Catalina 30. However my wife and I lived and cruised a 51 footer with enough room to install a gen set, water maker, 2 a/c units. 120 and engine driven freezer, refrigeration, crisper combo. Sold her in 2000, bought a condo in St Croix and the Catalina 30.
I registered the boat in Florida. Boat registration is about where the boat is and has nothing to do with what State you have your residence in. It all depends on how long you are going to be there. Before my boat wasn't even registered as I kept it in Mass and they didn't require a coast guard boat documented boat to be registered.
If you stay in Florida a certain time you need to register there. At the same time be doing it I didn't have to pay the yearly excise tax in Mass. My boat wasn't registered inany State, which also could be a problem in some states if I stayed more than 30 days.You have to pay sales tax if you owner the boat less than 6 months, which applied to my dinghy.
I bought it in St Martin, Caribe and it was very basic.. and tiller steering. All I had was a tiller pilot and I bought a spare battery and a 40W solar panel to keep it charged.. this was dedicated to the tiller pilot. My escape boat was an old Avon roll up inflatable I kept half inflated on the fore deck. Apart from speed and depth log and the boats compass that was it.. oh..!! and an early Magellan hand held GPS.
Pick the best time of the year and you should be fine.. its a downhill run with wind and current behind.. only hard bit will be the windless zone before Panama so load up with spare jerry cans to extend your motoring range. Another tough bit will be beating N to the Bahama's. Hope this helps, feel free to ask more if needed..