This one's easy.
Buy the one you fall in love with! I know that sounds a little simple, but the previous posters are all correct- You know best what you want out of the sailing experience, and you are the one who has to judge which boat will meet your needs. My wife and I looked at several boats before we bought our first. We knew that we wanted a trailerable, weekend-capable, well-performing boat. We fell in love with the Hunter 23, and bought it in less than a week. It met our needs at the time, but after moving to a new sailing area, it wasn't up to the task anymore. The new sailing grounds needed a heavier boat, with week-long vacationing ability. Also, standing head room and an easy sail plan were high on the list, and we had a place to keep it in the water. A fixer-upper was OK, as we now had maintenance experience... As we were shopping for a new boat, we fell in love again- with the Hunter 25. When I go to the next place where I can keep a sailboat, I'm sure that I'll be looking for another one to fall in love with, all over again. One other thing to keep in mind- At the time I was shopping for a boat, SailboatOwners.com was just HunterOwners.com- Actually, it was Phil Herring's own personal web site (and web development experiment, I suspect ;o). They hadn't even started Planet Catalina yet. At that time, I saw the value of having this kind of support network, and having that network of owners to advise a newbie was quite a strong influence in our boat buying decision. With the new sites on line (for Beneteaus, Catalinas, C and C, MacGregors, and O'Days), There are quite a few more folks out here to help with whatever model you choose.Good luck with your decision!--Jon BastienH25 'Adagio'