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I have a '74 S21, with winch in the compression post. i have never had the pin, nor cable apart for repair. I sail freshwater, mostly with the keel up, and the boat in the water the full summer season each year. So I do not have first hand knowledge of the repair.
I believe you have to chisel out the filler material covering the ends of the keel pin. You can probably leave it on the trailer for the pin, but would have to raise the boat for cable work. I have thought about changing to a trailing edge cabel, rising to the cockpit, or just inside the hatchway for reduced strain on the cable. I doubt I will ever actually do this as it has some disadvantages (weeds, vibration, etc). If I were to try it, I would glass-in reinforcing material at the hull penetration point, terminating in a tubular upright nipple. Then attach a flexible hose to the nipple, high enough to clear the waterline. I would carefully consider the angles and abrasion points at the penetration port. Good luck and keep us posted. Perhaps others will answer your question from actual experience. There are a lot of "keel disaster" veterans on this forum.
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