So the thing I’m stuck on is that the entire OP is, as far as I can tell, largely restating the OSR ethos and then going “so how would this work in 5e / scenarios that would break it.”
-you are expected to look at the game world and dig deeper, using player knowledge and ideas.
-skills generally barely exist, those that do are aligned with very specifics classes.
-creative solutions, generous GM info, and “roleplaying” (as in: acting as your character and having them interact with the world, not funny voices) are held paramount over any mechanics.
-consequences for failure are baked in: time and resources.
So, it works (with a hefty dose of GM fiat which that play culture umbrellas under “rulings not rules”). I think a better question is: if I did this in 5e, what systemic issues might my players raise and how would I adjust for them.