Best time to buy
Theoreticly winter would be best, people are cold, and the romanticisim of sailing is less when it''s pounding rain outside. That being said, my experience (what little I''ve got) has been that the best time to buy is when the boat you want is available for the price you want.
I started looking 2 years ago for a boat. Had to be small, cheap to maintain, sail well, be seakindly, be in good condition, and be under $1000. Once I added that last one in there, it became a very hard boat to find. I just waited, kept my eye out, and talked to people. 4 months ago I found a beutifull little 20'' sloop, with a 7 sail inventory, in awsome condition with nothing but first rate equipment (lewmar winches, ulman sails, all stainless rigging, etc) for exactly a grand. She''s now mine and she''s a pleasure to sail.
You can sail what you want, when you want, or for how much you want, but you only get to pick 2 of the 3. Just keep your eyes out, and if you''re looking for something over about 27 feet, dont be afraid to look all up and down the seaboard, as getting it to New England wouldnt be that hard.
Wishing you fair winds and following seas.