I have been stepping the mast solo since I bought my boat in '85. There are only 2 things I need. One is a simple tripod made from some old tent poles and the other is a length of line about 8' long. I set the tripod up behind the trailer and set the mast on it with the base at the front cross bar so I can pin it. I never disconnect my shrouds or wires but coil them and tie them to the tramp while trailering. I tie the 8' line to the end of the jib halyard and to the bridle at the forestay adjuster. Its purpose is just to extend the length of the jib halyard. I raise the mast and lean into it as I reach down to uncleat the jib halyard. I pull the jib halyard tight and cleat it to hold the mast up and then fasten the forestay. Since the tension holds the bridle up, there is no problem with the forestay reaching the adjuster. I found this method described many years ago in an article in the Hobie Hotline.

I have timed myself and can usually set up the boat in 20 minutes alone. I think it takes longer when I have help.

Howard