Re: rain water entering bilge thru mast.
Happens here as well. However, it became a serious problem the first winter I had the boat. It filled the bilge and backed up to the genset locker and then froze solid.
I now remove a thru-hull near the base of the mast and it acts as a drain during the winter. In my case, it happens to be an intake for the head. Anything in the path of the ingress would work.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.