Yes, mast stepping is the hardest part of rigging and de-rigging and is as much an art as it is hard work. After you do it a few 100 times it will get easier <img src="http://www.catsailor.com/forums/images/graemlins/smile.gif" alt="" />.

A few suggestions:
I used to secure a milk crate on the back beam to secure the mast to the rear beam for transit (with a pfd on it) and to give it some "lift" for putting the pin in the hinge. It required me to sit on the mast while pinning it.. but it worked. I still needed help lifting the mast.

I would NOT use the shock cord (attached to the traps) to secure your mast for side to side motion... I would use trap wires with lines arround the beam tied off through the loops on the end of the wires.

or purchase a mast stepper for about $175. I used to use one on my hobie 18. the mast was a beast. The stepper is a pole that attaches to the mast and uses the winch to pivot the mast. It takes a while to set it up, but when you get it working... it is good for self stepping.