Primer pockets usually give out before you get case head separations.
Another problem I ran into that brass will "normalize" after a while. You size the brass down, it has a memory of the chamber it was fired in. So, it can expand back out after a period of time. For this reason, it is a good thing to use brass that has only been fired in that chamber if you want to let the ammo sit around for a while. So, using range pick up brass, or brass that has been fired in a large chamber can cause problems down the road. I have seen this in 270, 7 Rem mag, and 300 Wm.
It is not unusual to push the shoulder back .006 in order to get the web dia to a point where the bolt will close easily on some factory rifles. Brass spring back is a bitch.
Best to keep your ammo fresh if you are using brass purchased once fired or range pick up brass. If I am shooting ammo loaded last year, I will cycle all rounds though the chamber of my rifle to make sure there are no "tight" cases. Obviously, I have a lot of brass purchased once fired from test rifles. When I shoot this brass up, I will NOT buy anymore.
Same kind of thinking would apply if you have several rifles of the same caliber and you are not keeping the brass separate for each rifle.
You hear of guys talking all the time about not pushing the shoulder back more than .002, but you have no idea if the web of the case in that chamber is within spec of the dies you have on hand. Factory rifles's web dimensions can give you fits. So, don't be surprised if you push the shoulders back .002 and you still have a hard time closing the bolt. Just keep adjusting the die down in 1/16 turns, then check and see if the case will chamber. THEN, measure and see how much the shoulder has been pushed back. If it has been pushed back .006 or more, then just watch the area in front of the web for a bright line forming, indicating that the case is about to have a case head separation. At one time, I had various lots of brass Rockwell tested for hardness, and there was a 12% variation between brands of brass and a 6% variation in hardness of the same Lot. I was not testing Lapua at that time.
Soft brass is going to loose primer pockets sooner and tend to have case head separations in factory chambers.
The best shooting factory rifle I have ever owned was a Browning Stainless stalker in 7 Rem mag. With a muzzle break and 36x leupold(load development only)I could shoot 140's in the 2's, three shot groups. The chamber was egg shaped, and I had to push the shoulders back .009 on every full length sizing to get the rounds to chamber properly. Rem cases would last 5 firings.