I used to be really paranoid with my Glock and not reload more than 5 times. Now 15 seems fine as long as it's watched. I'll toss cases with even minor damage. I also avoid Remington brass because the mouth is thinner and doesn't crimp the same as other brands.
I usually lose the brass before it get's reloaded too many times. Of course as some point I just say. "Ah, I'll just leave these, they're getting old anyway." Rather than pick them up again. I usually do sweep them up and toss them away so other reloaders don't mistake them for once-fired and pick 'em up.