In mid range 9 mm loads I have been getting about 20 loads using Federal Champion. I don't know how many loads above that I will get from Winchester yet. Different manufacture's cases will give you different results. Loading them hot or near top end will reduce the number of reloads you get quite a bit.
I have had a couple of cases crack under 20 loads. There were very few of those. I have even had a cracked case with the Winchester and S&B case. Keep the expansion of the mouth to a minimum and you might find the cases last longer too.