Finally got around to tearing it down. We also learned it's not the original motor, was repowered sometime in the 80s or 90s.
Discovered milkshake underneath the intake. Suspect the intake gasket went bad and leaked coolant.
Poured gas on both cylinder heads to test for leakage on both heads. All cylinders would leak - some on the intake side, some on the exhaust side and some on both. Pulled valves on the known bad head. At least one intake valve is completely shot, the others are borderline.
Need to figure out what destroyed the intake valve(s) and be 100% sure what caused the coolant to get into the oil. Hopefully just the intake gasket.
Crank turns over nice and smooth, used a socket extension and hammer to test each piston for knock, everything was solid. Cylinders look maybe a touch questionable with slight surface rust, but they are smooth to the touch.