I passed by a 23' MacGregor the other day because I was convinced (she convinced me) that it would be too much for me to single-handedly set up, launch, sail and take it back home. Any opinions?
I got to say, even if it is physically possible to step the mast on this boat by yourself (and I'm sure it is, though you might need some sort of a gin pole system)-- that's going to be a lot of time spent not
sailing just to go for a day sail.
If keeping a boat in the water is not an option, I'd at least look for a place to park the boat on the trailer near a launch ramp so that I wouldn't have to step the mast and rig the boat every time I wanted to sail.
With what you propose above, I think most people would do it once or twice and then say forget it because it's just too much time and hassle. In my situation, if I can get a few free hours from my wife and son on a weekend, and if they don't want to sail, I'm at the boat in 15 minutes and underway in 5.
Are you retired?