I did the keel on my C22. I bought a $50 floor jack on wheels first. I welded up a simple U bracket that fit in the hole on the floor jack swivel which made handling the keel a piece of cake. Not only did I lift the keel I also lifted the boat with it to take the trailer out from under, and put it back again. I used it in my shed to lift and flip the keel several time as I worked on it. I used it to lift one end of the keel and back my van under it. I placed a piece of pipe on the van floor as a roller, then lifted the other end with the jack and rolled the keel into the van. Unloaded it in my shed the same way. I put the keel back on the boat with it. Did it all safely, with no one helping me at any time!
I have a quick cheap fix for the enlarged keel pivot pin hole. Lay the keel on it's side. Place a piece of waxed 3/4" PVC pipe through the hole in the location where the pin hole belongs. Use putty (electricians duxseal works well) on the bottom side of the keel to hold the PVC pipe in place and seal the hole around it. Pour a glass filled epoxy mixture around the PVC pipe level with the top side of the keel. Once it has set completely, hammer the short piece of PVC out. This leaves you a pin hole with a diameter of 1.050" which is perfect to allow some slop so that the pin and brackets don't see any bending load from the keel, only. They only hold up the weight of the keel.
So maybe it doesn't last forever, it only cost $20, took about an hour, and can be redone as often as needed.