I load for several calibers and I load to where they shoot best. Usually this is at the upper end, but that is because I put the bullets real close to the lands and it does create more pressure, so you have to be real careful and always work up your loads. All my guns shoot real awesome, but it takes time. Now to answer your question, I find that the primer pockets get to loose before any other part of the brass shows signs of unreloadability, you still have to bump the shoulder back and trim to length as needed, nothing drastic like burnt powder marks or anything just not a good friction fit like the first couple of times. So, I would say that is around 4 times. With that said, I throw out the magnum loaded brass at 4 times anyway. Just my own safety rule. The lighter stuff I throw away after 5 to 6 times. All brass and loads are not created equal, so it depends on many variables. That is why a good step by step processing system is so important.