I would also suggest a Catalina 25. I have looked at a few and hopefully will have one of my own soon. The company is still in business and there is a large member's association, so help and parts are not far away. Another to consider would be an O' Day 25 or 272. Older boats and no longer being made but have heard good things about them. On the trailerable side, a 25 is more "transportable" as opposed to be a true trailer-sailor. Mast stepping and rigging it can take time and some effort but, can be done with 2 people. Good luck and welcome to the asylum!
EDIT: There are Hunters out there too that would fit your requirements as well. The newer Catalinas and Hunters have wing keels instead of the swing but, you are going to pay more for those.