Ok, I had to reread the original post to make sure I think I understood...
Agreed... 22 foot is probably the last sized trailerable I'd consider day sailing FROM a trailer.
I've owned a Capri 14.2, a Capri 22, and a Capri 25 (the 25 is the racing boat lighter than the Catalina 25)... I like the lines of the Capri 26 (it's a nicely laid out cruiser).
I day sailed my 22... solo. It took about 1 hour to setup, and 1 hour to tear down. I only did it once, and I was pretty good at it when I did it (had the boat for over a years when I tried it). It was the easiest trailerable wing keel boat (draws 2.5')... I could launch it without an extension, it self centered on the trailer... and I used an A-frame to raise the mast myself.
Now I am WORKING towards setting up my 25 footer with a 4' fin keel to self-launch. it's too large to do without strap launching (or an extension)... I use the same A-frame to raise the mast. I figure I'll be doing pretty well, if I can get it launched for this season in under 2 hours. The 26 is bigger/heavier (slightly shallower).
I slip my boat from May to Oct. It's the best money I've ever spent on my boat. I don't have my boat on big water (because there is none close by)... I instead put it on a lake where I can get to it quickly (45 minutes is quickly)... when I get there, I am sailing withing 10 minutes flat. WORTH VOLUMES to me!
Consider long and hard how you will use your boat.
By the way, my 14.2 Capri was a 3 stay rig, and my best time launching was 30 minutes.