Ovinomancer
No flips for you!
Well, yeah, but what I specifically meant to ask was how you, personally, use your discretion as a DM to determine under what conditions to call for a Perception check from a sleeping creature, and under what conditions the answer to the question of whether a sleeping creature does or doesn't notice some element of the environment is certain.
An example was given up-thread of a situation in which it was uncertain whether a sleeping person would wake up when another person snuck into the room and removed a book from a tall stack of books in order to borrow it. I said I might resolve the removal of the book by calling for a DEX (Sleight of Hand) check with a DC set depending on how difficult conditions make it to complete the task without making some sort of comotion that wakes the sleeping person. I would only call for such a check provided there's a meaningful consequence for failing the check, however, e.g. the sleeping person might not allow the book to be borrowed if awakened, and the book would have to be acquired in some other way. A similar approach could be used with a DEX (Stealth) check to see if the borrower's movement through the room awakens the sleeper, but again a meaningful consequence would need to be in play.
What I wouldn't do is contest either of those rolls with a WIS (Perception) check from the sleeping person because an ability check resolves the outcome of some effort on the part of the creature making the check. A sleeping creature is making no effort to notice elements of its environment, so in my book it shouldn't be asked for a check to resolve such an effort.
I agree, and as a DM, I like to keep things simple for myself. The game gives me two pieces of evidence relating to how aware sleeping creatures are of their environment. First, as I've already mentioned, is the Elven trait trance which strongly implies that non-elves are less conscious than semiconscious when they sleep, a state that I would regard as unconscious, and for which I would impose the Unconscious condition, which specifies that an unconscious creature is unaware of its surroundings.
Second is the sleep spell. One of its effects is to impose the Unconscious condition. Now, one might make the argument that the condition is imposed only in the case of magical sleep, but I would think that what is particularly magical about the spell isn't the quality, or depth, of the sleep imposed, but that it puts you to sleep when you otherwise wouldn't have been, and that its effects resemble mundane sleep in most, if not all, respects, the main difference being that it can impose sleep during combat, which seems to be intended.
Yes, I'd throw perception in there too. An unconscious creature is unaware of its surroundings, and a creature's WIS (Perception) check measures its "general awareness" of its surroundings. So if the creature is unconscious there's no need to check its perception with respect to its surroundings. We already know what the outcome is.
It's a bit odd to call part of the game's rules text a "ruling", and I'm not trying to get into a debate about what the rules should be, but you are of course free to rule these things as you wish at your table regardless of what the actual rule-book says and in accordance with what makes sense to you. The way it all makes sense to me straight out of the box is that a creature only has one awareness with which to perceive its environment, just like it has only one WIS score. It can choose to occupy that awareness in a variety of ways, but once occupied for an exploration round, or whatever interval of time we're concerned with, it cannot apply its awareness to any other task that requires it. So creatures who have occupied their awareness with exploration tasks other than keeping watch for hidden threats (which are often resolved with a WIS (Survival) check, btw) don't have the option to also use their awareness to keep watch for hidden threats.
A trancing elf, on the other hand, by virtue of remaining semiconscious, has a partial awareness that he or she can apply to keeping watch, albeit at disadvantage, provided the elf's partial awareness is not otherwise occupied. For example, the DM might allow elves to trance while walking and performing other sorts of exploration tasks as well, if need be, because the meditative trance only takes up part of the elves' awareness. It's one of the things that makes elves special.
But what ends the unconscious condition? The rolling of initiative? Surely it's not the loudness of combat, as they're unaware of such things in their surroundings. If the sleep spell imposes normal sleep, then it surely takes an action to awaken from sleep if attack, yes?
In reality, how you play your game is your business, and I certainly wish you all the funs. But there's a serious logical disconnect in your presentation here.