A long and careful search
My purchase of a 1979 O'day 23 was the result of a lot of research and legwork. I never owned anything larger than a Sunfish, so when my wife and I time-shared in a Catalina 22 for a year, we got to see what we liked and didn't like about "bigger" boats. I came up with a list of must-have features, and started looking. I knew I wanted a boat no bigger than 25 feet since I wanted to keep maintenance, dockage, and all other fees down to a minimum. I also realized that I would be mostly daysailing in protected waters, with the occasional overnighter, so I favored a big cockpit over a spacious cabin. I liked the idea of a centerboard (easier to save yourself from a grounding), but didn't like the idea of all of my ballast hanging by a pin and a wire. My wife also wanted a separate head compartment so that she and our guests could pee in private without having to close up the companionway. I saw a lot of boats and scanned a lot of ads, but it seemed that I would have to compromise on at least one of my criteria. Then I visited a broker who had a couple of O'day 23's in the yard, and once I saw the boat, I knew it was the one for me. I had never seen or heard of it before, but it had the separate head, the keel/centerboard combo (something I had only seen in the Rhodes 22 before), and a large cockpit. It only remained to find one that was in good shape with the other high priority features I wanted (bow and stern pulpits, lifelines, anchor locker. About a month later, I found "Biloxi Blues" through an ad on the internet. She was on the hard for the winter when I bought her, so I did not get a chance to give her a sea trial. A little more tender a sailer than I would have liked, but generally an easy and forgiving boat. Her maiden voyage was in 20-25 mph winds, so I know that even though she heels early, she she is ultimately a stable boat for her size. I also know of at least twice that the centerboard has saved me from a grounding.