Answering this homebrew question reminded me of the peculiar nature of the sleep spell -- on level one, it is an absolute beast: common opponents like kobolds or goblins have around half a dozen hp, so the 5d8 hp sleep effect on average removes three or even four of them, with a single action and no save. And even removing a single opponent with no save is pretty impressive.
However, the spell quickly becomes less useful as you gain levels and your opponents have a lot more hit points. It still can retain some usefulness, for example for finishing of mobs or monsters that have been softened up with a fireball or other attacks by your party, but eventually you stop preparing it.
My question here is -- at what level is the actual turning point reached, at which the spell, upcast to the highest level available, can be expected to lose usefulness to put to sleep (a) multiple opponents and (b) a single one?
Clearly, this will vary a lot based on the individual opponents. You can encounter goblins when you are level ten, or an ogre when you are level one, and it may retain some use for those weaker opponents you run into for a longer time. For this question, please assume opponents in the form of monsters whose CR matches the average party level.