I stabilize it by standing on the tramp while someone cranks the winch. It really doesn't take any effort to do either. I'm not sure it would do a lot of flopping around even if I cranked it by myself. Maybe if one side of the boat was raised higher, the mast would stay all the way on one side in the process.
Once it's up, and the shrouds are tight, the winch has enough advantage to connect the forestay, and not have to bother to retighten the shrouds after. It's a pretty small winch too.
With the A-frame on the trailer, there is nothing to rig, other than raising the A-frame, and snapping the hook onto a couple of trap wires. The A-frame pivots on the front crossbar, and will go down behind the bridle wires. In total, there is one connection to have to do for the rigging-the forestay.
A roller on the rear mast carrier makes the process easier too-both ways. It's a urethane bow roller for a boat trailer. You can roll the mast forward, and backward pretty easily to either attach it to the step, or get it back on the front mast carrier.
That trailer also has an easily detachable system for carrying the second boat above, with no weight, or contact on the lower boat. There are four bolts, and a change of the mast carriers required, but it's not really that bad to switch from a single, to double carrier. It went all over the country. I built it in 1988. It's hot dip galvanized, and still looks like the day the parts came back from the dipper.
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