I bought some PVC to make a DIY mast stepper.... But then I tried to lift it all by myself and was able to set it up and down all by myself.
For me, 6'4", 250lbs, and a reasonably strong young adult I'm able to raise it manually via brute force. It's so fast that I've decided to forego finishing the mast stepper. I can raise the mast in 1 minute manually, would needing to spend time setting up the steppers, or winching. This was especially useful yesterday, when due to overhead power lines, the only place I could raise the mast was ON the approach to the boat ramp. Nothing makes motorboats impatient like watching me run lines while blocking their precious ramps.
What I do - Raise mastI have a safety line that runs from the forestay, under the front crossbar, to the mast support on the trailer (through a CamJam) and back to me. Once the mast is 100% up, I pull all the slack out and it's fine.
What I do - Lower the maskI reconnect the safety line to the forestay, run it under the front crossbar, to the mast support on the trailer- (NOT through the CamJam) and back to the Jib Cleat on the main-crossbar. When I am ready to lower the mast via brute force, I brace the mast with my weight, and leg spread, and yank up to release the jib cleat. This frees the mast, and lets me walk backwards in the most dangerous game of 'trust the trampoline' in the world.
If I had an assistant (my wife), I'd:
1) Ask her to raise the mast the first few feet while standing at the mama-bob. The first few feet is without a doubt the hardest part.
2) Ask for the assistant to run to the front and pull on the safety line as I raise the mast. This reduces the work I'd need to do, and also makes sure there is no chance for the mast the fall between me getting it upright, and grabbing the safety line. (I'd explain thoroughly how the CamJam works before executing this plan)
If I didn't have an assistant, and didn't want to kill my back before I'm 31, I'd:
1) Use a ladder, as others suggested, to get the first few feet of raise.
2) rest the mast on the wing/bench, then lift it from that position.