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I would fix the problem (leaks) instead of drilling holes.
There are multiple entries on this site and others as to the location of common leak areas. (rubrail & moulding in engine well - all 4 stay plates - front pulpit, mostly wire enty hole)
While actually sailing "I think" I had some water entry up through the swing board cable "pipe." Which I recently extended slightly higher by reclaming the existing hose slightly higher (used some sealent also) as well as adding a pvc fitting for more height. I also used a piece of a sponge as a "baffle." Haven't been in the water since I did this.
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