I'm trying to finish repairs on this boat. It's almost ten years old and this is the first real maintenance so I can't complain. Poked a hole in it a month ago. That hole is now ready for final patching. I glassed the outside of the boat a week ago. Now the inside.
But I discovered an area of wet wood at the base of the stem where my trailer hitch eye bolt goes. I know better than this but didn't do it anyway 9-1/2 years ago when I first built this relatively flat bottomed lake boat.
It's not a good idea to drill any holes through fiberglass, through wood and then on out to the other side in any area that ever gets wet.................without drilling it out way too big at first, filling the big hole with putty and then walking away. Then come back the next day and drill your 5/8" inch eye bolt hole in the middle of a 1" inch epoxy putty plug. Then you won't get wet wood.
I know better. I have done this the right way many times before. But didn't on this boat and now I'm paying the price. So I ground off some fiberglass. Drilled the hole out to 1" inch wide and now I have to wait 2 - 3 days for it to dry. I'll leave an electric fan heater on it for a day or two. Then I'll do it right.
Still. After nearly ten years this boat is still in very good shape. It wouldn't have needed much work at all if I hadn't crashed the front end into the corner of my trailer, under power with a 20hp Merc. Maintenance once every ten years isn't a bad record.
Anyway. Drill those eyebolt holes out way too big. Fill the big hole with putty. Then re-drill again with a smaller bit. Then you won't get wet wood.
...also, for what it's worth about eyebolt holes in the stem, I like to put them way down low so the boat jumps up onto the trailer roller by itself. I like to load my boat by winding the winch handle, without having to walk around to the back of the trailer to bust a gut lifting the front end of the boat up onto the roller.
But if you do that you'll have a wet hole. That needs to be built the right way.