Muddyboots - thanks for your comments.
My .223AI barrel is a Bullberry. I am using a FL sizing die, I have it set at the point where it leaves the case the longest. I am resizing about half of the neck, likely not even hitting the shoulder. Any deeper and the brass comes out shorter, and the headspace is shorter than the back of the barrel. As it is set, it is as near flush as I can get it, but there is clearly no brass outside of the barrel. It may still be too short and causing this primer problem.
I've gone from camming the die over, all the way to barely touching it, this is the longest I can make it. Any suggestions?
As for the worn firing pin, I haven't done much dry firing, but this frame has thousands of rounds through it with a few dry firings, I was thinking of replacing it anyway. Where is the best place to buy one?