You trim when the case gets too long based on measurement with a caliper or checking with a gage. Then trim about .010" below max. What else could prompt you to trim?
So far, I have had good luck by triming to .01 under max. case length. I have to do this every single time that I fire that case. I am reloading .300WM so maybe these get stretched more than a non-magnum case, I don' t know.