TLC vs. Almost new
Last year, when I was shopping for a C22, I saw boats that were made in 1980, and boats made in 1990. Believe it or not, the boat I ended up buying, a 1981, was in better shape than many of the late 80''s boats. Once a boat is 5+ years old, the maintenance it receives will be the difference in the condition.
My advice is to only look at boats that are in ''excellent'' condition. IMHO, you are better off with a 20 year old boat in sail away condition than a 10 year old fixer upper. I paid $4500 for my 1981 with a 1994 trailer, engine and sails. I had to NOTHING to do except sail it. In the spring I tuned up the engine, sanded and painted the keel and launched it. When bigger-boat-itis set in, I sold the C22 for $4000, and the new owner absolutely loves the boat.
Take your time, look at lots of boats, and when you find ''the one'' you will know.