I've never found any limit to the amount of times you can anneal and work a piece of brass - some of the formed sheet brass buttcaps I've seen on originals have been worked quite heavily. Brass will age harden with time, which can't be annealed in my experiences, but with that exception you should be able to work the brass almost indefinitely. The moment you start feeling it get hard or springy again, anneal it. It's that "one last bend" that will crack it. For shaping the long bends in a brass patchbox, I use a concave maple form that the brass can be pressed into with a vise.
-Eric