We have a 1990 MacGregor 26 S that we have owned for 4 years. It's great boat but a pain in the butt to launch and retrieve. We plan on 2 hours to go from travel ready to sailing and vice versa. I keep it in a slip most of the time on the Illinois River but a couple times a year we take it to either Kentucky Lake and/or the Great Lakes.
My personal goal is that we stay a week or more before I consider it worth all the effort. I have streamlined everything I can think of: Genoa stays on the roller furler which stays on the mast, main stays on the boom, 9.9 Merc stays on the transom, bimini stays on, etc. I have the latest mast raising system with the gin pole and brake winch. It still takes 2 hours...
That being said, by keeping it in a slip just 10 minutes from work, I get to sail at least 2 - 3 times a week with no effort at all. When we take it on vacation, we live on it quite comfortably. I installed a C-Head composting toilet which is great but since it doesn't have a shower we usually stay at marinas along the way.
Since we sail the Great Lakes, I consider a 26' at the lower end of safe for those size lakes. Yes, they say that if you are a good sailor you could sail around the world in a bathtub with a sail, however, theres the whole comfort and safety thing...
Hope these few thoughts help!