Trailerable and seaworthy... trying to find a compromise

MacGregor 26 : Safety - MacGregor Sailboats® | MacGregor 26 Official https://macgregorsailboats.com/macgregor-26-safety/

 

Here is a link to a unique trailer sailer. I discovered it after starting to build my own design closely resembles it and many (I think) of your SORs. I believe I would have tried to track one down if I wasn't already building my own boat.

https://www.chuckpaine.com/pdf/24bahamasandpiper24.pdf

I would definitely modify the mast to some kind of hinged tabernacle design to make hoisting a one person task. One of the design goals with my trailer sailer was to have a similar set up time, but conflicting SOR requirements puts the set up time. If I had a taller storage area, I could work some hinged tabernacles into the equation and also devise a way to safely highway the boat with the sails bent onto the masts. My build blog is here.

Blackrock 24 (Build) https://www.boatdesign.net/threads/blackrock-24-build.46526/page-23#post-855539.

I've done a fair amount of trailer sailing with my other boat and a 30 minute set-up is not unreasonable. Especially, if you spend any amount of time sailing the boat once it's set up. On of the problems with your (and my) list of SORs is that the size, accommodation and capability requirements take the boat out of the light, daysailor category and put it into a heavier, more complex boat that needs serious forethought and design to simplify its set-up to only take a few minutes. My current goal is the thirty minutes. I have yet to set up the rig from a state of being previously rigged, so stepping masts at this still involves some extra steps at this point.

In meeting your SOR for a quick set-up, I think the two most important components would be am easily hoisted rig that is accomplished single-handedly (as I believe you already stated) and being able to transport the boat with the sails already bent to the mast(s).

Best of luck in your quest.