This is something that I would also be curious to learn more about. I have often heard that for rifle ammo, you should count on say 3 to 5 reloads and should check with a sharpened paperclip when you see any sign of a "ring" around the case head.
My personal experience with 30-30 and 30-06 is much, much higher numbers of reloadings, but I don't load to "max pressure" loads on anything.
My "gut" feeling is that how much you need to "trim" brass to the proper case length after each firing, is a clue as to how much the brass is probably being redistributed away from the case bottom or base (case head separation).
I have never had a case head separation, but I have thrown away brass with cracked cast necks and primer pockets that seem sloppy and large.
I am now doing some reloading with Winchester metric 7.62x54 R brass and doing a little more case trimming than I have been use to with other cartridges for near full power loads, so this question now has my interest. (Although, I am now switching to reduced cast bullet loads, so I expect that the amount of trimming will start to slow down a bit.)
As to pistol loading of brass, gosh, I have reloaded a bunch of 9mm, 357 mag, and 32 acp so many times, I have lost count. I have looked at trimming the brass on these handgun cartridges and found that after the initial case trimming, the is hardly ever a need to shorten them. Again, very seldom, do I load to the maximum pressure.
I seem to crush the rim on more cases by not belling the mouth enough for jacketed bullets during the bullet seating operation than I loose to case neck splitting. But I have to toss a few away because the neck splits. Again, no case head separation ever and I have some 32 ACP S&B (cheap brass) that I have reloaded maybe 50 times or more.
I suspect that if I were reloading Weatherby Magnum rifle rounds, things might be much different.