Backing plates
Brad - This isn't a direct answer to your question, but earlier posts have covered that pretty well. Adding to Tom S's comments, you should consider a backing of some sort for just abt. ANYTHING that you bolt thru or fasten to a f'glass laminate. The idea is to eliminate the point loading or hard spots by spreading the loading over a larger area. I'd use marine ply as Tom has: remember to radius the back side to match the curvature of the hull & give it 2-3 coats of unthickened epoxy to seal it from moisture. I'd bed it to the hull with thickened epoxy, but I guess a good grade marine caulk/bedding is OK too. If your hull is cored where the thru-hull is located, the recommended 'drill' is to remove a bit of the core material around the hole and replace it with thickened epoxy, to seal the core from water and future rot problems. This may not have been done by the manufacturer originaly as it cost $$ and takes time. None of the holes thru the cored deck of my O'Day were sealed this way and there is some core deterioration at almost every opening as a consequence: fortunately my hull is solid glass, so there are no issues there. The caulking/bedding compound you apply cannot guarantee that a tiny amt of moisture won't get thru in time. I'd use 3M-5200 below the waterline, but Main Sail's comments abt. Sika have got me thinking & I'll check out their products in future.