Brass stretches the most when it is new. I count on all cases, in all calibers, needing to be trimmed after the first or second firing. Often they will need to be trimmed again after the fourth or fifth. After that they often don't ever need to be trimmed again.
If you are using range brass there is one type, can't remember the headstamp that has a roll crimp that needs to be trimmed every time. it also only wil take 3-4 feloads before failure.