Catalina 27 or 30
I own a Catlina 30 and used to own a Cal 27 and have sailed on numerous Catlaina 27s. Maintenance is the same between the two. For cruising, you''ll find that the layout is essentially the same, but the 30 has a lot more general room. You really can have a half dozen people on the boat for a weekend and everyone will have room to actually stand at the same time. It''s got something which is rare in boats, which is open space. The 27 is the same, but simply lacks some of the open space, which makes it more difficult to have several people on board for a weekend comfortably. The boats are similar sailing, except that the longer waterline makes the 30 a little less prone to "hobby-horsing" in a steep chop.
Hope that helps,