I've reloaded some brand new Winchester brass 15 times now or there abouts, I've lost count. I started with full power loads, but have since only used them for trailboss loads. My reason for that is because the brass cannot hold a heavy crimp. Using 700gr bullets on the 4th shot the 5th round comes out past the cylinder and locks things up.
That Winchester brass was large pistol primer brass I reamed out to large rifle if that matters. The primer pockets are a little bit looser, but still plenty tight.
I also have some hornady brass going the same amount of reloads, maybe a bit less. I have tried annealing them once. And it helped a little, but I've never annealed before.
One problem I have been having is when the cases stick (to much pressure) the cases actually stretch to the point that the case leans to one side when on a flat surface, it gets ironed out once I resize.