What we found out in the shop: 1) starter can be too close OR too far away. You have to push the gear in mesh with the flexplate to see what gear contact you have. We've had to mill starter nose before! 2) stuck centrifugal weights on a HEI distributor or any distributor for that matter means someone over advances initial timing to compensate. That extra 10 20 extra initial timing is REALLY hard on flywheels. Good luck!
I've seen busted nose cone before any flywheel damage. Simple solution, toggle switch the ignition so engine can wheel up before ignition is introduced.