Mike, I also think that's a great idea. I wonder what the length of the support would have to be for it to work.
I sail a H16, so the mast is pretty light... Maybe you guys are right. I'll just stick to an old mainsheet mounted to the trailer. I didn't really consider the slow retreival speed of the winch, but now I see that it pulls only about 6 feet per minute! I figure that from the mast base to the mast tang is about 16 feet, that means that you'd have to pull roughly 20 feet of cable to get the mast up... You would be standing there for about 4 minutes with "the remote in your teeth".
jrg