Thanks GreenLake,
I was able to pull the bolt out last night and get a better look at it. There is definitely something missing. I agree that this setup looks like it should slide to adjust mast rake but there is just one single hole and an empty void under the keelson. And because it has been used in this configuration for what I imagine is quite some time the bolt has caused damage to the mast jack. You can see in the pictures below that it has blown out the side of where the bolt goes through. There is a small section of the keelson around the opening that also has week fiberglass, which will probably need to be fixed. Plus with all of that weight on the bolt for who knows how long, I am wondering if the glass where the bolt was supported is structurally sound.
My initial thought was the mast jack was probably original, it seems to have that late 50s look and feel to it. Then at some point they re-worked the keelson but did not set it up correctly.
However, the keelson itself looks to be original fiberglass work as it seems pretty solid and the transitions to the hull seem solid.
Comparatively, there are signs of poor fiberglass work around the cb trunk and under the cuddy. It looks so bad it reminds me of plaster of Paris ... It looks like someone just dipped some fiberglass in resin and the layed it down and left it... oh and then painted over it... no prep work what so ever and no sanding afterword... so that is all peeling up.
So perhaps they just tried to find another mast jack that would work and set it up in this bizarre way. I can't imagine someone thinking that a 1/4" bolt could support all of that downward force
Based on all of that I am not confident in trusting the previous work that was done to this boat... so unfortunately it looks like this project just became much more involved than I was planning. I know that is par for the course in boat repairs but still frustrating when I wanted to get her back in the water pretty soon.
Either way I have to decide how I am going to engineer a solution for this keelson and mast jack. I think the mast jack itself could be salvaged if I have someone drill another mounting hole on the opposite end... it seems to be symmetric on both ends.
Not sure there is room to glass in a support structure under the keelson without opening that up some more.
Perhaps there is a way to retrofit something on top of the keelson to replicate the system that you have setup?
Going to think through this some more while I work on other aspects of the project.

- Resize_20220727_073422_2184.jpg (109.7 KiB) Viewed 1899 times

- Resize_20220727_073420_0705.jpg (112.77 KiB) Viewed 1899 times

- Resize_20220727_073418_8999.jpg (62.96 KiB) Viewed 1899 times