I dropped my keel to do the keel rebuild by raising the trailer and boat on jacks, building supports under the boat, then lowering the trailer. I built the 2x6 and 2x4 supports in place, once the trailer and boat were raised. I used auto jack stands to support the trailer and hydraulic bottle jacks to raise it.
The stern was supported by a bench like support that spanned the hull and supported it from the transom forward about 16 inches. Closed cell foam cushion the hull.
The bow was supported by a pedestal about 24" by 24" square built from 2x6s and 2x4s that was built in place between the trailer frame rails. Two bunks cushioned with closed cell foam supported it just forward of the keel pivots on either side.
I never removed the trailer, just lowered it and rolled it forward enough to lower the keel. The keel support kept it from flopping around while I replaced the pin, supports and cable and trailer bunks.
The pin hole in the keel was worn only about 0.05 to 0.08" so I left well enough alone and never bored it out to install the bushing. There's some play but it's much better than before especially with the shims installed on the front of the keel.
When I get home I'll post pictures. The boat is down on the trailer now but I still have the supports. Cost about $ 75 worth of lumber, bottle jacks were $25 at HF.
It was a little tedious, raising the rear, jacking it, raising the front, jacking it, then back to the rear again but it was rock solid even though my driveway has a slight pitch.
If I had to remove the keel, I think I could have slid it out the rear but that would have required helpers and some sort of a rolling frame to support it. As it was, I did the whole job, rebuilding the keel, replacing all the keel parts, keel support, cable, turning ball, volcano tube, keel winch, trailer bunks, trailer winch in four days by myself. That includes reinforcing the keel winch mounting with aluminum and oak supports. The hatch threshold was cracked from trailering with the keel raised.
The only problem I ran into was that I don't know how long the cable should be. I followed the instructions that came with the winch but it looks to me like I've got way more cable on the winch spool than is necessary, about four to five full turns when I think the keel will be fully lowered. Anyone know how long it should be?
Hopefully, by the time all that stuff wears out, it will time for a new boat.