I currently load .243, .270, .30-06 and .300WM. All are Remington brass. I don't believe it's any better or worse, it's just for consistency. I don't anneal at all. Most of my loads are heavy, but not super hot. I've never had a primer pocket issue. .243 may start to get small longitudinal cracks in the neck after 5-8 times. .270 seems to stretch a little bit each time, but goes on forever (12+ times) with no signs of head separation. .30-06 doesn't last long because it's an autoloader; if they survive getting beat up and lost, they may start to show signs of head separation after 4-6 times. When I first started loading .300WM, I did full-length resizing and the cases only lasted 3-4 times; I changed to partial resizing and they now will go 10-12 times.

I believe your rifle chamber dimensions have a lot to do with brass life. If it's oversized or long, brass life will suffer. Of course, hot loads add stress to the brass as well. You can extend your number of loads by annealing and/or partial resizing, neck-only resizing or just bumping back the shoulder, providing they still cycle properly.