OK, solved the problem.
Long story short, the RCBS seating die that I previously thought was not a taper crimp die, was. That was messing up the shoulder as it over crimped. Backed the die out about and 1/8" from the shell holder, seated a new bullet in my dummy case, and it had no issues. It solved both the chambering and seating problem. Needless to say, Im used to Hornady rifle dies that do not have a taper crimp unless you buy them that way. Even still, totally my fault, and I put 2 and 2 together after I talked with a buddy, and we talked it over and he threw out some ideas. In short I should have RTMFM!
A couple pics
From left to right : once fired, sized, dummy, factory, and another reload. The only one that had issues was the dummy. Everything else chambered, even the once fired. Do you like my dykem in a marker? I figured the Magnum 44 is worth a laugh at least :)
You can see the shoulder hitting the chamber wall here where I marked it up.
Now some case measurement number for nerds:
Before I hit on the fact that the crimper was screwing me. Shoulders measured with Hornady 375 comparator
Once Fired:
OAL: 2.542
Shoulder: 2.120
Shoulder (across): .495
Sized:
OAL: 2.540
Shoulder: 2.115
Shoulder (across): .491
Dummy
COAL: 3.300 (wanted to see if this long COAL would hit rifling, it did not)
Shoulder: 2.108
Shoulder (across): .496
Factory
COAL: 3.043 (shorty round nose bullet)
Shoulder: 2.102
Shoulder (across): .488
Overall, lesson learned!