Just remember....All of the boats with swing keels or centerboards have one thing that you need to check out that can be hard to check out....The swing keel.
I had a Hunter 22 and if I knew then what I know now I would have been pretty paranoid because I never checked the centerboard.
As for my Hunter 22...It was a great boat. It was a good design and I sailed it for some longer cruises. I crossed the Chesapeake Bay in it. It is a little tender but it sailed well in light to moderate winds.
Where I sail, the Chesapeake Bay, you can get some big weather. The wind and waves can get up there. When I downsized I went to the Compac 23 because I thought that it would be a stiffer boat. 23 foot boat, 4500lbs of displacement. It doesn't have a swing keel but a centerboard. It is a pain to rig but I can do it. It takes a fair amount of water to launch.
That being said, I have already sailed through 20 knots upwind on it for a while and I am happy with my choice. It takes the chop well, sails well, and has a great set-up and layout.
My Compac 23 would be quite comfortable for two people for a few days, bearable for a family for an overnight. A huge thing is having a separate head. I don't have it and it is very nice to have so you don't have to move things to get to the head.
I have no experience with Macs. I know that the Catalina 250 and Hunter 260 are both good boats. I personally know people who have had each of these boats and they are good. Heck, if I was going to spend the money, I may have gone after a Hunter 260.
If budget isn't as tight, another really nice trailer sailor is the Seaward boats. The Seaward 26rk looks like a great boat. They would be the most expensive route but they are well done. There are some Seaward 25 boats out there that are starting to get in the area of reasonable when it comes to price.
There is special maintenance for the water ballast. The owners can fill you in on this but it has to do with the ballast tanks. There is maintenance for a centerboard and they can be a pain if you sail where there are barnacles and you leave the boat in the water. Again, there is why I went with the Compac because I don't have the centerboard issue, the ballast is in the keel, and I may leave it in the water for the season.
If you are wanting to daysail, the stepping and unstepping of the mast will be an absolute pain in the butt. You will be spending a lot of extra time messing with that and it takes away from sailing. Drysailing one of these boats would be a good set-up and I have considered that with my boat (I am also dependent on the tides where I am and there aren't any places in my present location to dry sail but I know of another marina in my area where I can do this and it is something I am considering). You avoid bottom paint, barnacles (if you are in salt water), and other land issues. You just launch and retrieve each time and store with the mast up.
Really work on your list of what you want to do with this boat. Even better, experience other people's boats. Volunteer to help people step and unstep their mast. Books are great, but they are lacking hands on experience. Find sources to get some of this real world experience for yourself so you know exactly what you are looking for. No matter what you spend, a boat is a big investment. It may not much cost that much initially, but you are also investing in your safety, your leisure time, and your sanity!
Also.....Talk to Crazy Dave. He can help a lot!
