Jeff H help me out please.
I think this is a pretty difficult question. How you plan to use the boat is a bit mutually excludive when you talk about a 30 footer. Thirty feet is quite small as a live-aboard boat, especially of this is your sole residence. It is alos a little small for the time of prolonged voyaging that you are suggesting. It''s not that it can''t be done; its just that long range voyaging is just plain harder in a 30 foot boat.
If I were looking for a boat for your venue and purpose, in addition to your criteria, I would think some of my primary criteria would include (in no particular order);
-Good ventilation (temperatures can get quite warm even in winter but there is generally enough of breeze to keep things bearable if you have good ventilation.)
-comfortable motion (the Gulf Stream and the shallow banks of the Bahamas and the Keys really can make for some uncomfortable seas. Comfortable motion is hard to achieve in any small boat so a boat with a good hull shape and not too blunt a bow is helpful.)
-the ability to carry good ground tackle, (There is a need to anchor reliably in a wide range of conditions is especially important as these venues have a lot of different bottom conditions.)
-a way to carry a dinghy on board (This is too small a boat for davits and towing a dinghy behind a small boat in the open tracts of the Bahamas is a good way to lose a dinghy and perhaps endanger the parent boat.),
-good water and fuel tankage,(While the Bahamas have really become quite developed compared to even 15 years ago, water and fuel are not exactly around the corner nor are they at US prices.)
-Good storage,(no matter how small and simple the boat, you need to be able to carry enough supplies and stores for you an the boat and a 30 foot boat is just not big enough to allow you to indicriminately carry spares or extra supplies.)
-4 to 5 foot draft (more than 5 feet draft can inhibit the places that you can get into in the Bahamas and Florida Keys. Less than 4 feet of draft can really impact sailing performance negatively. I really am not a fan of shoal draft wing keels especially in the type of venue we are discussing.)
-a fair turn of speed (probably a PHRF of 174 to 180)(This may seem irrelevant but there are areas where the anchorages are pretty wide spread in the Bahamas and it is dangerous to approach these areas (or even sail) at night because of the coral heads. A slower boat has only two choices; motor flat out or anchor out in an exposed area. Even as little difference of 20-30 seconds a mile can make a big difference. The motoring issue is a big one on a small boat where you don''t have the kind of motoring range that a bigger boat might have.)
-a good seaberth somewhere near amisdhips (because a 30 foot boat is by its very nature slower than a bigger boat of the same displacement there will be more times when you will end up anchored in less than perfectly hospitable locations. Getting sleep in those conditions is hard enough but it is especially difficult trying to sleep in the ends of the boat where greater motion and slapping is more a problem.)
Now obviously not all of these can be achieved in a stock boat so what ever you buy will need some modifications. You may also want to condsider a larger boat.
In no particular order, some posibilities are:
-Tartan 30 and Tartan 34''s (Both are favorites of mine)
-Cal 34, Cal 31
Hunter 30 (1979-81, We have had two of these in our family and they have been really good boats for this kind of thing. They are up in age these days and so you are looking for one in good shape and that has been upgraded.)
Niagara 31 (really good boat for your purpose)
-Pearson 303 (a little slow but otherwise good for what you want to do), Pearson 35 (venerable keel-centerboarder but not at the top of my list), Pearson 10M (a little deep and short on ventilation)
Sabre 31 to 34
I am sure there are more but I need to get to the office.