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Looking at O''''Day 23...comments??
I have had an ''83 O''day 23 for about 7 years and absolutely love it for bay sailing. The main things to look for are the coring of the deck where the chainplates go through and the condition of the bulkheads. The chainplates tend to leak, which if not tended to, can cause the bulkheads to rot. Both can be easily repaired by yourself if the deck isn''t in too bad of condition.
I don''t recommend this boat as a typical trailer-sailer. The mast isn''t easy to step. It takes about an hour, by the time you have re-tuned the rigging.
During the first year I had my boat, I stored it at a marina, on the trailer, with the mast up. Now I keep it in the water which has proved to be much better.........more time on the water.