Not a dumb question.
Always after sizing. Straight walled cases have a tendency to be
longer after sizing than before, depending on the amount that
the diameter needs to be decreased. I don't have much experience
with rifle cases but I would imagine that if you full case resize
that it would have the same effect. It may not matter if you neck
size only.
Rifle cases, after resize. Straight wall pistol cases I have NEVER trimmed them.
RCBS makes their X dies which supposedly, after initial trim to specs, you NEVER have to trim for the life of the brass. I used them and sold them off. They worked the crap out of the shoulder of the casing and after three sizings, I started getting case separations in my 5.56 AK. I think they were really designed for bolt actions, much more gentle on the brass.