Given your location, I would join a sailing club and work with that for the time being. Once the season ends, spend the winter looking for a boat that you want.
I look for boats year round and, in my experience, the best deals pop up around October and April, with some scattered in between, but there are fewer in the summer. If you just want to sail, join a club for this season and learn to sail, maybe see if people will let you aboard their boats and look around, so you can get a feel for what you want (it'll change a lot at first...), then make a list of boats you like and spend a few months looking. If you have the cash on hand and are patient, you can find great deals.
I look for boats year round and, in my experience, the best deals pop up around October and April, with some scattered in between, but there are fewer in the summer. If you just want to sail, join a club for this season and learn to sail, maybe see if people will let you aboard their boats and look around, so you can get a feel for what you want (it'll change a lot at first...), then make a list of boats you like and spend a few months looking. If you have the cash on hand and are patient, you can find great deals.