I recently bought my "first" sailboat. Though I had grown up sailing small sailboats at the family lake cabin. My first is a 1984 Hunter 25.5. Sailing out of Milwaukee It was not difficult to look at a huge variety of boats (used). Many were out of the water and would require a large investment to get these boats seaworthy. I was looking to stay under 10k and get as much boat as possible. I was willing to have a pro survey any boat I was making an offer on and was prepard to do most of the work myself.
What I did was identify how much I could budget for the purchase (cash), storage, repairs, outfitting and dockage. I found a boat that I was able to deal on.
But getting all the facts on paper of what you want in a boat is more important than picking what boat you want first.
My wife wanted headroom, I wanted a boat that was fun to sail, had an outboard, and was capable of boucning up and down the western coast of lake Michigan with confidence. There had to be a buyer eager to sell. The boat had to have potential and score well in a survey. I found a Hunter 25.5 that filled the bill nicely. I would not say this is my ultimate boat nor would I think it is more than it is. A light coastal pocket cruiser. It has really exceeded my expectations. A fun boat, sails like a
dinghy (may be a bit tender for some) but get her up to speed and she stiffens up nicely. The
rig is sized so that I can have one hand on the tiller and the other the main sheet like a
dinghy....
So far this season we''ve made the Milwaukee - Port Washington run - 26 miles one way lots of sailing out front in a variety of conditions and have been getting used to learning all the things about larger boat ownership. In August we''ll be heading south for two weeks bouncing down the coast to Chicago. Sailing during the day and overnighting in the many ports along the way.
I say find yourself a used neglected boat in good condition of a reputable model that is known to your local sailors. Set your expectations of how you will use the boat and lay out REALISTIC goals. Have any used boat surveyed first!!! It is way worth it!!
Good Luck
See you out there