Hey everyone-
So, I finally got around to getting the ladder off and making the repair. No wonder it was leaking- I'm surprised it wasn't leaking more. In the first picture you will see the holes in the boat were large, and had absolutely no sealant in them at all
So, we reinforced the inside with exterior plywood and reinstalled the ladder with lots and lots of 4200 to take up all the extra space in the mounting holes. I also used a Dremel to widen all the cracks in the gelcoat and (you're gonna hate this part) in the interest of getting back on the water filled the gaps with 4200. It's a bit messy looking, but it's an old boat and I only lost one day on the water. Depending on how much it bothers me I will cut/grind it all back out once the season ends and do a proper gelcoat repair.
We've been out on the water several days since the repair was made and there's absolutely no leaking
Thanks again for all the help