A few years back I did a shoot to destruction test on 50 pieces of Winchester 45 Colt brass. After 50 reloadings (two hot, 48 plinking loads) I had 25 pieces left. Took the last 25, loaded with Pyrodex, shot them, then trashed them. In 45 ACP I'm sure I have some with 100 times through my dies, just never bothered to check in a controlled way.
Bottle neck cases vary tremendously. If loading 303 Brit, two, maybe three times is my limit due to the generous chamber in my SMLE. In my Garand I do about five times, trimming after the 2nd and 4th loads. Each rifle/chamber is unique as is the brand of brass, some may get more loadings without splitting or a suffering from a case head separation, some may not.