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I owned a Catalina 22 for many years -- wish I still had it.
You'd be pretty tight with three adults, but it could be done (more like a camping adventure than comfortable cruising). For one or two people, it works great. If you end up with a 22, I would find one that was 1985 or so, when they had the slide out galley. You stick the galley in your garage and use plastic bins instead. Lots of storage for such a small boat. This model will give you the forepeak berth, a loooong narrow berth on the starboard side (where you took out the useless galley) and a little bit wider berth on the port side (with the table down in the berth position).
I would try to go for the 25, if you can find one in your price range.
I made a gin pole type of contraption to raise and lower the mast. It usually took me about an hour to get launched -- some claim they could do it in 30 minutes. The mast on the 25 and 27 are, of course, larger, but with port and starboard supports (to keep the mast from swaying as it goes up), I'm sure something could be contrived to raise and lower the mast. (After I did it three times, I rented a mooring and only did it at the beginning and end of the sailing season after that. It's a pain, and you will not be able to just say, "hey, I have a couple of free hours -- think I'll take a little sail. )
These are great boats and will take a lot of pounding, but they are not designed for deep water cruising. As long as you have a sufficient weather window, you can coastal cruise some of the more remote areas, but you need to plan and be willing to wait or cancel your plans if the weather is not 100%. Otherwise, you need to be within reach of a protected port/harbor at all times.
Good luck!
David
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