I have seen brass reloaded more than 4 times with win or rem brass, with moderate hunting loads. However, the hotter you go, the less brass life you will see is a general rule of thumb. Also, the more you work the brass through firing and sizing, the less life the brass will provide.
The points below are areas you can check prior to loading. I think some of these still apply to pistol brass but not sure as I do not reload for pistols.
For rifle brass, look for incipient case head separation and loose primer pockets as tell tale signs that your brass is past ready for the bone pile. Case stretching is normal for bottleneck cases. As you trim, the brass you are trimming is coming from the web of the case (google incipient case head separation). This is an area where heaspacing may be an issue. Proper die setting is critical to maintaining brass life and over doing it could get you to separation faster.
When seating your primers you will "feel" some resistance in the process, when that resistance goes away, you are entering the bone pile phase. This happens faster with hot near max pressures. I have noticed loosend primer pockets with one or two loadings with fed or rem brass with near max loadings.
Case hardening is a normal process for brass. You may notice heavy sooting, or seating bullets becomes harder with the number of loadings. All of this could be associated with brass hardening. The final result of hardening is brass failure such as neck splitting or case separation. You need not go there. Toss them in the bone pile or learn to anneal your brass well before this becomes an issue. Elky.....