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So one of my issues I need to fix while the boat is on the hard is the "Wallowed Out" bolt holes. Looks like original from 1981.

On the inside I was considering roughing up the fiberglass, creating a dam and pouring some slow cure epoxy (Table Top Stuff - up to 4-inch pours) to "Fill the Void" back there. BAD IDEA???

I find myselfe to have a similar problem. While underway in light sailing some water find its way from the transom area into the bilge.
The only suspects are the lower gudgeon and its bolts or the bolts holding the sterntube.

Are your gudgeon bolts in the bilge/transom are? Hard for me to get a good loock since a modified diesel tank is blocking my view. And it also seems to be a solid area with epoxied play wood in between (check picture) Or it might be the sterntube bolts, since I had them loosened last winter while installing a new prop.
Might as well reseal all of them.
I am welcome to any suggestions.

Last summer, before taking the boat out of the water, I climbed-low crawled ect to see. I removed the hot water heater which made it easier. I was thinking the packing gland but ruled that out. Next was the stern tube but once I got back there it was obvious the grudgeon bolts were the culprit. Righr now is the time to fix since the water heater is gone along with the motor. Lots of room to fix things - kinda of.

Another source might be the just above water line thru hull drains. Exposed constantly they can crack and leak. Worth checking even if they aren't the culprit. They have a 15 to 20 year life.

Sorry I haven't gotten any photos. Will do so tomorrow when I head down to the boat...

What’s that pipe/tube thing next to your propeller?

It is a cable protection for an older sonar/fish finder and will eventually be removed.

Last weekend i was inspecting the leak further while under sail and found the culprit.
I was crawling head first into the portside storage locker only to discover the leak right in front of my eyes.
The cockpit drainage (square hole through the transom above water line) was badly laminated on the bottom side. Only one Layer of fiberglass which apparently did not stick all the way to the side. From the outside it was covered with gelcoat. Now the gelcoat got a crack right on the spot that always has a bit of water remaining in the drainage. So every wave splashing into the drainage will leave a bit of water, which seeps through the crack into the bilge.
Never would have thought the leak would be there since it looks very solid from the outside.

Will "seal" the crack with duct tape for this season and repair it properly over the winter.

Sorry for crashing this thread.

I got sidetrack the last few days. Shiney red thing showed up today. Will take a few photos soon.

Looks beautiful! Congrats!

So here is the culprit location. The pintle bolts have wallowed out their location and now the hole is an oval. Busy at work. I like OT but its to the point that I'm sick of it and rather have a few days off.