Do you have an example comparable to the OP that shows how it would be resolved in 5e D&D?So, I'm going to cite D&D 5e as an example of a game with a granular resolution system based on setting -> situation that works.
My familiarity with 5e is only passing, but I am aware that there is quite a bit of contention about the proper working of the Hiding rules, which might come up in this sort of example.
If I wanted to provide an example of granular resolution, based on setting => situation, working reasonably well, I would provide an example of a classic D&D dungeon crawl. In that sort of scenario, the setting is established (via map and key) in sufficient detail for effects specified in 5' and 10' increments to be applied; there are well-understood ways in which setting leads to situation (opening doors, wandering monsters, or some "tricks" to use Gygax's jargon); there are relatively clear rules (ie movement rates) for correlating changes in position with the passage of time; and the architectural details that a map tends to foreground as elements of the fiction are highly salient to the goals of play.
There are some parts of the classic D&D rules that are not smooth in their interaction - thief hiding, other PCs hiding, surprise rules and invisibility are the most obvious/notorious. Cleaning these up shouldn't be too hard, though. I imagine there are OSR-ish games that have done so.