I anneal mine after the every fourth loading, and have some on their at least 20th loading so far. I don't load 30-30 hot anyways either.
Wow! I don’t load anything, but I don’t get that out of 357 mag brass. I’ll look into annealing then. Is there a method you use for that?
I make it a habit to anneal every 5th firing you need to be cautious not over anneal because this also can be bad and make brass brittle.
How "loose" the chamber the rounds are being fired in.
If you firearm is new and has a minimal chamber size the brass will be stretched less than in, say, an old rifle with a more worn chamber. Typically something like an old Winchester 1894 will have a sloppy chamber. They were made that way in order to cycle with whatever ammo got stuffed into them. Add in long use over many years and ta-da, a loose wollered out chamber. A more modern rifle such as a Marlin or H&R will have a tighter chamber.
This causes excessive brass stretch thus shortening case life.