I will check the core rot in the transom, I have yet to tear into that area yet. I have a big core rot project on starboard side under the mid ship stanchion. It was not properly sealed and took out a good chunk of the hull.
I also have bow deck area rotted out a little bit due to the cleat not being sealed.

Anchor locker area is solid

Bulkhead around chainplates are also solid.

Starboard winches core is rotted a little bit, that has been removed already.

Will talk to my sail maker about adding slugs on the main.

Thanks for the notes on rudder and keel. I think the keel will stay the same way, not even sure how to lengthen one. I am thinking about making a balanced rudder that would be 16 inches deeper.

Also have a crushed core in spots under the sail tracks and some of them are corroded. Would replacing them with slightly longer ones gain anything?