Take this summer and don't buy a boat. Buy lessons. Learn to sail, and while you do, you'll be looking for boats that interest you. Do some ASA keel boat stuff and sail small boats if at all possible... yes, the little ones that tip over.
Shop in the fall and buy after the winter storage has been paid for. Machiavellian for sure, but you'll know more, get a better deal, and be able to sail your new boat in relative safety next summer.