Catalina
I agree with LaDonna about going with what you like, but temper that with what your needs are.1) Do you plan on overnight cruising or mainly daysailing?2) Are you sailing in open ocean, coastal, inland lake, or backyard pond?3) How much do you want to spend?4) Do you want something that's trailerable or something more substantial?5) How many people are in your family that you need to accommodate or do you mainly singlehand?6) How much time do you want to put into maintenance?7) Is the older boat that you are considering still supported for parts?8) Inboard or outboard?9) Do you plan on racing?10) Are you handy or will you farm out most of the work?The list goes on and on, but you first need to decide what kind of sailing you plan on doing and then go out and find a boat that will best fit your needs. I know a guy who started with a Catalina 22 and then went to a 30 because he wanted to do more extended cruising, but after owning the 30 for a couple of years, he is still primarily just daysailing and singlehanding. He now wants to move down to a 25 because he doesn't need a 30 for his needs. I own a Catalina and one of the selling points for me was the fact that parts for Catalinas are readily available no matter how old it is.