I don't know Particle, the 'A' frame idea sounds good for an occassional mast rigging for a bigger boat. I would think as a frequent way of raising and lowering the mast (plus the transport of said A frame) would be a real PITA. The keel stepped mast is more complicated than a deck stepped in terms of regular transport/rigging everytime you want to use the boat. It would be VERY nice to have the boat at home after each sail, but I see no easy solution...maybe someone else will come up with an idea.
Personally, I would make up my mind and pick a primary sailing area. Then find a marina or storage at water's edge and dry sail it on the trailer (rig up). Then just hook up to the trailer and launch. It'll cost more than home storage, but would be a good option and a lot less hassle to rig every time. Good luck.