At 59 and having to trailer it all the time, I normally go solo a few times a week. I also have to unhook my shrouds at the side chain plates along with the trapeze bungees in order to remove my mast from my trailer each time in order to get everything to fit in the garage. (Homeowners Association rules).

When I am setting up, I leave my boat tied down on the trailer and put ~5' tall tripod about 10' behind the back crossbar to support the mast before I pin the stepping hinge with a phillips screwdriver. Next I connect a 6' piece of rope to the hook on the end of trailer's winch strap and lay it and the hook on the tramp next to the mast base. After hooking up the shrouds, I raise the mast by standing on the tramp with one foot on the back crossbeam. When the mast gets up to about a 60 degree angle, I slide my left hand down closer to the bottom of the mast and pull back with it while pushing forward with my right hand. This allows me to guide the ball at the base of the mast properly into the mast step. After the mast is up all the way I lean into the mast with my shoulder and I reach down and pick up the 6' piece of rope (that is connected to the winch strap hook) and wrap the rope around the mast above a cleat I installed about ~5' up the side of the mast. Next I tie the end of the rope off to this cleat (on the side of the mast). With the mast securely upright, then I can use the winch to pull the mast forward a few inches so the shrouds are almost tight which is enough to connect the forestay to the chain plate. After that I uncrank the winch so the forestay is now holding up the mast and then disconnect the 6' rope from the cleat on the side of the mast and go from there.

To take the mast down, after I have pinned the stepping hinge, I tie the 6' rope around the mast above the cleat and connect it to the winch hook. Then using the trailer winch I crank it a turn or two to create slack in the forestay before removing the chain plate pin. I hold the mast upright with my shoulder while I untie the 6' rope and then lower the top of the mast onto the tripod. Since I have to remove the mast from the trailer when I get home, I disconnect the shrouds and bungee cords for the trapeze lines. Using 6 small bungee cords, I strap the shrouds, forestay, halyards and trapeze lines to the length of the mast. Next I unpin the stepping hinge and walk around to the middle of the mast and pick it up and walk it forward around the side of the tramp to support it on the Y post above the winch.