Hey Nick ... I just bought an O'Day Daysailer. I live in Lexington. I'll be sailing my boat at Cave Run. I also joined the sailing club at Cave Run. This is also my first sailboat, so I don't know how much help I can be. The sailing club could be a good investment for you. I think it is $75 for the first year and includes a beginning sailing course. The course is pretty basic, but worth it. It's 2 evenings in class and a half day on the water.