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I sort my brass by headstamp, just so things are consistent. When I first started reloading, I was sorting by number of firings. That went out the window as an impracticality, because everything I reload for is semi-auto and when brass gets flung, you always end up with brass you didn't shoot in your pile. I do always inspect each case. This is pretty easy, since I sort by headstamp into separate bins anyway. I do plan on sorting by number of firings for bolt-action brass. I'm planning on starting into 7.62x54R, as soon as I decide on what diameter bullets I'll be loading.

As for pistol brass, I think I've had one case crack in the past 2 years, and I'm pretty sure it wasn't a case that came from my stock originally. Generally they're more likely to get bent in an unrecoverable way by being stepped on at the range than to wear out.

For rifle brass, it's pretty easy to tell if there are problems with the case. I reload .223/5.56 and the only way I've had them go bad is from a split neck. This usually shows up after firing or after resizing. I've had a handful of cases do this in the past year that I've been reloading rifle brass. I don't have any system for throwing out rifle brass, I just throw it out when it cracks or is otherwise damaged in an unrecoverable way from being stepped on.

For those that are significantly bent on the wall but work themselves straight in the resizer, I will make sure to inspect the wall after resizing, as sometimes there will be obvious weakening there if the bend was sharp enough. If so, it gets tossed. This does not include the normal deflector dings that you get from brass ejected from an AR - those blow themselves back out at the next firing, to be replaced by a new ding at a different location.