Check the archives
there is some good advice to raising the mast. Speaking for myself and myself only.....I hated raising the mast, I didn't even try it myself. It was by far the worst thing I've had to do on the boat. Beating out lowering the swing keel for refinishing. AGAIN, just me.. The archives do have some excellent ideas in there. Some with nice pix and explanations and all. I have a crutch that lifts the mast around six feet up off the stern. I attach my forestay to my winch on my trailer, and while a volunteer cranks on it I lift and guide the mast up into position. It's real nice to get one other person who's job is to see that all shrouds stay loose and don't get hung up on something,ie the motor mount,the pop-top edges... I'm just one of those that if it weren't for bad luck, I'd have no luck at all.... Now I have a dryslip where I can leave the mast up. Figures tho, I'd forget to put the antenna up on top of the mast.... sigh......