I can't help you with the trailer issue, but I have a 1979 O'Day 23 and I love the way she sails. She is fast for her size, points well, and is very manuverable. The only complaint I have is that she is tender. In a stiff breeze she heels, and doesn't seem to stiffen until about 25 degrees. This can be alarming to small children, wives and non-sailors. I would check out the deck on this boat, as mine had some very minor delamination, probably due to stresses on the mast step. Also, look carefully at the stanchions to see if there are stress cracks in the decking at the bases. If you see any, check the surrounding deck and below for any evidence of water. One more thing to check is the fit of the centerboard in the keel. I have found out the hard way that centerboards can swell and stick in the trunk. See if the centerboard swings fully up and down. If it sticks, its not necessarily a big deal, but you may have to keep it partially swung out. This is what I do. Good luck.
