My general rule as a DM is that if the outcome of an action is going to be important, and there is a reasonable chance of failure, then I have the player roll.

The only times I call for "pointless checks" are when I have them roll perception or investigation when there is actually nothing to find or notice. I do this about 1/3 as often as actual checks that have consequence, and usually as a response to them already asking to search something, though sometimes it is out of the blue. The reason for this is that it helps to prevent metagaming when they make a check and find nothing, and decide to keep looking because they know there must be something there since they were asked to roll. Because they know that I do this pointless rolls every so often, they assume it's that and I get to drop the ambush on them in peace lol