Well the truck is finally good to go so figured I'd make an update. I swapped out the friction disc and pressure plate with some low mileage replacements, new release bearing, new pilot bushing, and I'm just gonna pretend I didn't actually see what kind of shape the flywheel is in. I also decided last minute to use a different trans I had sitting around. Was just about to put the trans back in and was setting the clutch fork/TOB in place and I noticed it didn't want to pivot smoothly. It would catch about halfway through the motion and it turned out to be the pivot ball was all chewed up on the end and had gouged the fork a bit. So I put the fork and bearing on the other trans and put it all back together. Still unsure what the exact problem was or if it was a combination of things but either way its problem solved.