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Doing a Similar Thing

I recently bought a 1973 ODay 22 (shallow keeled). Bought a new Loadrite trailer customized for it.
The boat has some minor, I hope, problems. A topside leak, or leaks, has watered down the two wooden bunk platforms. Having naugahide cushion covers on top of them trapped the water quite well. Over the winter, hope to make new bunk platforms. Think topside leaks sources may be the mast plate on the cabin, the window seals, andor the life line stanchion fittings. Any ideas of other things to consider?
Also some cosmetic considerations that a good cleaning and fresh paint should handle.
By the way, where are you? I am in southeastern Connecticut, and hope to sail Fisher's Island Sound, to and from Block Island, and in the Narragansett Bay region. That's why the trailer. So not stuck at one dock or mooring.
Look forward to hearing from you, or other that own 22's and read this. :)
 

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Has anyone heard of anyone ever drilling a small hole, from outside in, near the bottom of the shallow keel to permit it's drainage while being stored ashore for the winter? Of course proper sealing could be an issue come spring.
 
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