Welcome! I had a 22 for years, and moved up to a 28 last year. 22's become cramped very quickly, I'd suggest a 25 or the 27. I was nervous about the "big jump" to 28, but an hour on the water and I wondered what I was worried about. The bigger boat is easier to sail and a heck of a lot more comfortable Unless there are specific cost reasons (that is storage costs) for a swing keel and trailer, I'd go go with fixed keel. My experience looking 2 years ago was that a fixed keel was less expensive than a boat and trailer combination. That may have changed. There are no boat junk yards and getting rid of an unwanted hull is a challenge, BUT that fact can work to your advantage as a buyer! Just remember: the most expensive thing in the world is a free boat! Good luck!