1st warning: I'm in my third year of sailing and don't get out as often as I wish.
2nd warning: You're insane if you take any advice from me.
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I usually go out with my 9 year old son and my wife. We have a custom made trailer that has the benefit of being heavy duty but the draw back of being both ugly and very large. The boat sits over a standard 12" wheel and tire (call it 2.5' high), which makes damaging the boat while towing less likely (unless the truck in front of you throws a tread and you can't swerve because you are towing and it breaks a fender weld off the trailer shooting the bracing bar into your hull and then obliterates the tire, and of course the spare is flat and you have to ghetto rig the fender to not rub the new tire and your planned day at the lake is off) but also rigging more complicated. Did I mention it was baby blue and rusting?
Anyway . . .
Sales and dagger boards come off and go into the cat box. The boom is removed with "all the fixins" in place. But the rudders and all the mast lines are left in place. Where applicable they are stuffed in the port holes (careful not to kink them) or otherwise cleated tight. I take apart as little as possible but try to balance it with being a poor cat sailor and not destroying everything.
To raise the mast, I have found it safer and easier to use a winch. I have an extension at the front of the trailer that can raise 10' off the ground (so as not to just torture the mast while winching). Leaving the boat strapped to the trailer (and trailer attached to the vehicle) we move the mast into position and attach the step pin. I use 2 of the trap wires (one from each side) and attach to the winch line, the remaining trap wires are run out to the sides so as not to snag on anything. One person is on the tramp to help raise the mast the first few feet and then steady it as it goes up, the other cranks the winch attached to the extension on the front. The person who was steadying the mast liens on it a little as the person on the winch slaps the pin in the forestay (with the aforementioned do-not-use quick pin, which I may have to rethink), out pops the step pin and DONE!.
Then I remove the boat from the trailer onto the home-made cat wheels and finish my rigging. Throw up the jib and furl it. Hoist the main, pop in the boom, run the line and tie it off. Throw in the dagger boards, remember the tiller at the last minute, toss some bottles of water on the tramp, push her into the water and point into the wind. Then curse at some stupid power boater, complain that I chose the worst cove ever to put in at, find open water only to get to the middle of the lake and have the wind die, stop paying attention just as a gust flows across the water, learn the importance of quickly getting on the down hull to avoid turtling . . . get it upright and go sailing.
Down with the main sail. Off with the jib. Unpin the boom. Dagger boards and rudder into the box. Throw it back on the trailer. Trap it down. Reverse the stepping procedure for the take down, remember the mast step pin. Always remember the pin . . . Good times, good times.