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Garris -- alternative method for permanently waterproofing the drain and 100% preventing water intrusion.

Ernest -- I like your idea, but I would prefer to have the glass cure to the hull itself rather than "glue" it in afterwards with epoxy

I've seen instances with scuppers where people wet out glass around the hole and then inflate a ballon to keep pressure on the diameter of the drain while the resin sets.

Frankly I'm wondering if glass is required here -- simply coating the drain in epoxy would likely suffice.