Ritchard,
Wow, would love to hear more. I doubt we would go as far as you, but have been contemplating long sailboat stays in Winter.
Saint Martin continues to be the best, easiest place in the Eastern Caribbean to laze about on a sailboat - if you like it lively. There's a great yachtie community here, great services, chandleries, all the fun spots in the lagoon protected from weather. From here you can jump south or west or east to visit all kinds of different places.
However, the real golden age of cruising in the Caribbean seems to be over. All up and down the chain, there are more rules and restrictions, and new costs, such as mooring fees in lots of places there didn't used to be such. This had to happen eventually, it couldn't be a free-for-all forever, but some of the old-timers are pretty testy about it.
I wrote a cruiser's guide to Saint Martin if you'd be interested in reading it - PM me with your Email address.