I've launched solo from a boat ramp that had a small area next to it where I could pull the boat up while I parked. Same in reverse. There is another ramp that has no handy 'beach' area and I've seen another Wave us a small mooring buoy arrangement. I made one for that ramp, but haven't used it yet (old 25lb barbell plate, length of line, float, and hook). You just need someplace to have the boat be safe while you mess with the vehicle.
I also installed a winch on my trailer and that really helps with getting it back on. It's light enough that I could probably do it without, on a shallow ramp, but the winch was a good investment IMO and I think really needed on a steep ramp. The hardest part for me is getting it lined up and started on the trailer rollers, then hooking on the winch without it slipping back off again! Not a big deal.
Can't help with the other questions: I don't do mast up storage and I rake my mast back for med/high wind.
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