$.02
I bought a a 12 foot penguin and sailed it for a year. The end of the season, I swamped it and could not get back in. Lucky for me I was about 50 feet from the dock. Get a bigger boat. That was 7 years ago. Still have the boat.I next found a 20 footer and bought it, fixed it up, and never sailed on it. Scared I guess. Got fired. That was 6years ago. Still have the boat.So I looked to buy a bigger boat. I did a lot of research for that gem, the one that was enough to spend money on, but gave me a financial edge. I didn't know anything about pointing etc. Or sailing characteristics, sort of. I knew the mean size was 37 feet. I knew I might someday sail the ocean too. I bought a 34' Grampion, sight unseen. Or thought I did. The guy sold it from under me the day I arrived to pick it up. He gave me all my money back, and I saw the boat. Wow. This guy either never sailed her and kept her wrapped in a glass case or, as he said, he maintained her well. I was heartbroken, and started a new search. I called about a free boat in Wooden Boat, a 39' Dickerson, if I remember right. The old owner owned it for 40 some years and kept it in Bristol condition. His only caveat was that you be broke (or not rich enough to afford such a boat), and be a hands on repair person, and love woodies. I was second in line and he gave her to a guy in Omaha. Hope he still has her. The boat was valued at $95,000 to $120,000 according to the survey papers I saw. I am sure he could have gotten more. He did this because his children, who stood ready to inherit millions, were taken care of. But his baby was the boat, and he wanted her to go to a loving home.I found a 34 foot can't remember what that the guy was asking $18,000 and took $12,000. He was in the service and wanted the money and as quick sale. I missed it by hours. The boat was worth abut $25,000 according to the place where it was kept. My internet searched said the same thing. The place where it was kept said they had another boat for sale, a 37' Irwin. Needed some work, but was basically there. Asking price was $35,000. Way overpriced and out of my budget. He said she would take $25,000. So I put in a bid of $15,000. We settled on $18,500. After 5 years of ownership, I believe I paid $3,500 too much.I still have all three boats. I was told the 37' sails like a pig, can't get out of her way. But twice last year I was out and one time a new 39' Bennetau tried to catch us and couldn't. The other time was a Tartan, and they couldn't catch me. The speed is deceptive. I can and do take her out is 8 footers and not worry. She is slowly falling apart, but I finally got a job that is keeping me afloat. Actually I am saving some money. Not a lot, but a little. SO I can do repairs on her that she needs. When ever I tell my friends i want to sell her, they remind me that I have a condo on the water. SO now I go year by year. If I get rid of her, I will trailer sail the 20 footer till I die and probably never buy a big boat again.