There is a lot to see and do in the Bahamas but the winter weather is no where near as good as that further south. This was a particularly bad winter there as water did not warm up (one couple said they did not get into the water until April) and there were many cold fronts coming through. Further south, the only impact of the cold fronts was that the trades slowed down for a day or two (ie 10 knots instead of 20). If you have two years to spend you will be able to spend a lot of time in both the Eastern Caribbean and Bahamas (and places in between).
Particular faves for us were:
Bahamas -- Exuma Park, Staniel Cay (kids will love both Thunderball Cave and the swimming pigs), Georgetown for the family regatta but very crowded midseason, south of Georgetown it gets much less busy and we liked Long Island and Mayaguana
Elsewhere -- Puerto Rico (in general), BVI (beautiful but crowded), Montserrat (active volcano), Guadeloupe (especially Les Saintes), Martinique (St Pierre and Ste Anne), Grenadines, and especially Grenada.
There may be better places to buy a boat, check out BVI and USVI along with Martinique (reportedly there are something like 10 brokerages in Le Marin - how is your French). Be aware that there are issues associated with buying a European spec boat (eg 220v shore power setup (the wires are probably not big enough for 110v) and parts may be of very good quality but are brands not common in North America.
Heading back to Lake Ontario for this summer. Now in Bermuda and heading to Long Island Sound in the first week in May. Then on to the Hudson and the Erie Canal.