Bill,
I learned pretty quickly that heaving that mast up was not a good idea as well. I too use my trailer mast support but I have a winch with a webbing belt and a carabiner that I attach to the loop on one of my trapeze wires. Once the mast is handed to me, I support it on my knee and wait for my crew to get over to the winch. Once he has taken up the slack and gets it taught, I start to push up while he quickly cranks the winch. It goes very easy this way. Once it's up, I use the winch to tighten the rigging by continuing to pull forward on the trap wire while we attach the forestay. Works pretty well.