You have fretting damage on the shoulder that the timing pulley seats against. You can see it because there is a raised edge where it didn't wear that matches the slot in the pulley.

This is probably spacing the timing pulley too far back so that the damper assembly is seating on the front of the crank and not the timing pulley.

The woodruff key had worn that far.

To make your crank work, you need a timing pulley that fits flat on the rear lip and no longer drops into worn tooth pattern in the snout and gets compressed by the front pulley.

My recommendation is to replace the crankshaft.