i tried using a winch system and found that it really applies excess stress to the mast. i ended up breaking the mast base and then the cradle, which i didn't replce because of the difficulty i just reinforced it. now i will only step by hand.
i hook up the stepper linkage then have my girlfriend walk the end of the mast up until i can get it to shoulder height while kneeling on the rear of the tramp. (of course you want to make sure all your shrouds are staight and the shackel is tight...lay the shrouds so they are on the inboard side of the rudders so they don't catch). then the work is all in the legs. my girlfriend puts some weight on the base of the mast to make sure the stepper rotates corretly (incorrect rotation can cause undue stress on your base and cradle) and i just walk the mast forward. it's not that tough to get it standing, and once you do, forward pressure will keep it from falling sideways or back. i continue to hold it until my girlfriend can hook up the forestay.
you should have no problem. i'm not very strong and only weight 175 and have no problem.