At the risk of being a damp rag on this (because I think the idea of pitching it all and going to the Bahamas is a great one!), why the extremely short time line? What is your experience on a sailboat and doing maintenance
We are headed to the Bahamas this winter on our 28' Bristol Channel Cutter, which we have owned for 17 years and cruised on extensively for 3 years about 12 years ago. We decided in January of 2009 we would leave in October, and this still feels like a short time line - and this is on a boat we KNOW inside and out and doesn't need a whole lot of work. My husband can fix ANYTHING and has spent the bulk of the time since we decided to go doing the upgrades to radio
systems, making a new awning, etc.
There are good boats with solid bones that are worth the money
and time spent getting them ready - and there are boats you can spend money
on and might as well be throwing it down the toilet. Only you can know your capabilities, which translates to what kind of work you can tackle on board (which impacts budget)
Sorry to not answer your question, but perhaps knowing your boating
and boat maintenance
experience can help others answer the question more accurately.