Interesting. In these sort of cases I typically would use a primer pocket uniformer tool like the Franford primer pocket swager that would uniformly decrimp and correct the diameter of the pocket. I run all my military brass.through it. Works great.
I then follow up with a primer pocket depth...
Crimped primers almost never can cause this hard of an issue to deprime. The only way I experienced this is when I encountered undersized flash holes from some international ammo I didn't recognize. I've had the pin stick in the hole and had to pound it out from inside the case. That would...