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When you are resizing your brass, is the shell holder touching the die at the top of its stroke? (with brass actually in the die) A case that isn't quite resized all the way can jam in a tight chamber. Secondly, if you are trying to apply crimp a bullet with no cannelure, you could be distorting the neck and/or shoulder. It also does appear there might be rifling marks on the bullet, but that could just be the photo. If there are, you need to seat the bullets deeper. That by itself probably would not prevent a round from going into battery unless crimp was applied. I didn't see you mention if you tried pulling the trigger on that second round, but since you mention that you could not engage the safety, I take it that the round did not quite chamber fully and did not fire, nor would it eject. I would first make sure that you are sizing the brass as fully as possible, and if you still have problems you might need to use a small base die - at least when first resizing range pickup brass.
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