Originally Posted by SloopJonB
You'd have to be very good to put an SJ24 on a trailer in an hour or two. It would take that long to get the rig down if you didn't have a crane.
Sloop: IIRC, the SJ24 has a deck-stepped mast with hinged base plate, right? It's a fairly lightweight spar & only 3-4' longer than the rig on our SJ21, which I can walk up with one hand. It's usually ten minutes from hitting the parking lot to mast-up on our boat, Then another twenty minutes sorting out the lines.
The OP's real difficulty is going to be finding an affordable trailer and ramp-launching something like this:
But as I understand it, the PNW has lots of deep-draft boats: decent ramps, high tides, and an unusual number of owner-operated boat hoists. Tho probably not on the West side of the Island. The OP could maybe sail the boat there? A long sail, but an interesting one. There are also a few transporters with hydraulic trailers than can haul across the Island, including this guy:
Mostly About Boats: BOAT RESCUE PART 2: THE MOVE.
Don't be too horrified when you see the price estimate, tho -- professional hauling is not a thing I'd care to do seasonally! & A crane operator on site will ding you $500/hr.
It's a tricky thing. I'd not want to sail the West Coast of the Island on a swing-keel boat. Not personally. But a full-keeler certainly complicates overland transport. Still, people do it all the time, so it's not untenable.