You might try putting an oarlock on a piece of wood you can then clamp to the transom to find which side works best for you. I think it's a personal...
50 years ago that may well have been built with polyester, not epoxy. I'd definitely grind as much as I could and perhaps use judicious heat to help...
Keep in mind that an internal patch may keep water out of the boat, but it won't keep water out of the surrounding wood. If you want to save as much...