My system is pretty much the same as Howard's except I use A sports chair (it's off to the right of the boat in the pic below) instead of a tri-pod. I've been rigging my boat solo ever since I dropped the mast "with help" and that was more that 5 years ago. No one's fault, it's just that all the brains weren't on the same page. Thank God, the mast was not damaged.
I also use to rig the boat on the sand. Believe me, it's easier on the trailer. Although I use an Aussie halyard, I kept the original halyard (my boat's an 85) on the boat just for mast stepping purposes. Also, if you notice in the pic below, I trailer my boat with the beach wheels on the stern. By placing them there, they hold the shrouds toward the center so they don't get caught on anything while I'm raising the mast.

I also use the 8 ft halyard extension connected to the bridle as the standard halyard length isn't long enough to reach the bridle with the mast laying down. I do not allow help when I'm stepping my mast. I've also added a lance cleat at the bottom of the mast (for the halyard - I use it for both the standard halyard in rigging and the Aussie halyard.) to simplify the anchoring process once the mast is erect.
John, I leave the boat tied to the trailer during the rigging process and I always rig the boat on concrete (hard soil) before I move it to the sand. Like you, I use to rig my boat on the sand for the same reasons you quoted. I resisted this for about a year until a new beach cop began to enforce the "No rigging on the beach" rule. I was really upset at first but as I put the system together, it turned out to be a lot easier. Nevertheless, I say "use whatever system works for you." BTW, pinning the link is a breeze.
