RE: how many times?
Very broad quesiton.
300RUM, you get a good 3 shots before need of anneal and only get 2 more after that.
270win, you might get 5 shots before annealing and 3 after that.
44mag, target loads with unique, yo ucould get upwards of 20 shot before cracks. Heavy hunting loads, I am on shot 7 with a batch I have.
9mm, who knows.