Leak at shroud anchor

My friend's '84 boat is taking water in the port hull. We took a spray bottle with sudsy water, pressurized his hull with a cordless leaf blower and found significant leaking at the shroud anchor. Anyone know what he is dealing with here....delamination, stress fracture, what exactly? Can anyone recommend a short term and long term fix for this if any? Short term meaning get him through the summer without taking the boat off the beach.

Short term fix:
Remove the shroud anchor pin
Drill out the hole a bit (1/8") bigger.
Fill with chopped glass and epoxy resin.
After it goes off, drill out to spec diameter (I think it's 1/4")
Cut a couple pieces of fiberglass tape, one 4" long and another 6" long
Rough up the underside of the deck lip w/80 grit sandpaper.
Wet out the first piece with epoxy and lay it inside the deck lip at the anchor bar location. Do the same with the other piece, centering on the hole. (This is much easier to do with the boat upside down.) Masking tape on the hull at the level of the deck lip will keep oozes and drips from getting on the hull.
Before the resin goes off, poke a hole through the glass and reassemble the shroud anchor on the boat. Screw everything together tight.
After the resin goes off, trim off the excess.

You may be seeing the beginning of a hull/deck separation - that's why this may be just a short term fix. It'll stop the leak, though.

Thanks. I'll pass this along. My friend is also putting together a spinnaker rig for this boat. If this is the beginning of deck separation, will a spinnaker hasten the process? I suggested having longer anchor bars fabricated to redistribute the load.

The spin puts more stress on the boat, so for sure it's going to hasten the process - if something else doesn't break first.

While you've got the boat upside down, after you've done the fix, leak test it again, concentrating on the deck lip. If you've got leaks in the deck lip, that's a sign of possible hull/deck separation, especially at high stress areas like shroud attachments.

Longer anchor bars would spread out the load, but there's a point of diminishing returns - probably at or close to the length of the existing ones. Additionally, the curve of the hull makes longer bars problematic to fit.