Finally made some progess. ...or just gotten myself further into the point of no return.
Ebay transmission showed up. Looks good, no obvious wear, worn dogs, broken gears...
My back started hurting around here.
Looks like someone dropped a driver bit down in the starter box and said "oh well"
Split
Some metal flakes, sealant, and gunk.
Looks like someone has had this motor apart before. I haven't started tearing into the transmission yet but as it sits I don't see anything jumping out at me as a source of that grinding. Where would it be suggested I start looking for that random 4th/5th gear grind?