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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.
 

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Here some photos. Note that the keel shown was a lump of iron with rust 1/4" thick all over it. I started the rework by beating on it with the claw of a hammer for several hours! The hole was about 2" in diameter, and worn to within 1/2" of coming out the top. I rough faired it with body putty then applied 3 layers of epoxy and glass cloth over that and faired it again.
 

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You don't need to cut any holes to reach the pivot pin. The pivot pin is held by two brackets bolted up into the hull from the outside. You'll probably find that the bolt heads are just buried under bottom paint so you can't see them. Just support the keel and remove the bolts, and it will drop down pulling the two brackets with them.

Note that you also can judge how much pin wear you actually have just by measuring how far you can lift the keel with the jack right under the pin. If the keel only moves upward into the hull slot a 1/4" or so I wouldn't even bother to take it apart. Mine moved over an inch!
 
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