Can be done
I Have been rasing, lowering and trailoring my 1992 Hunter 27 for three years now. So far so good, with exception of some stress on my wife and a frayed side stay (see general interst post). I have some pictures to share if your interested, Ill dig them up. I purchased the boat and trailer already set up with this mast raising rig. I have to give credit to the previous owner for their enginering skills. Every year I try to tweak it to make it easier. Currently it takes 3 to 5 hours to raise, rig and launch the boat. As for towing, I admit I am at the limit (or beyound) with my half ton truck. Luck has it, I only live 5 miles from the launch.