One of the issues I have with these conversations is that we can never seem to just discuss specifics. We go from "how does describing how you climb a wall mean automatic success where rolling a dice means possible failure" to <poof> there's a rickety latter that can be climbed that was never mentioned previously. It feels like we either talk past each other or the goalposts keep moving.
So how about this scenario:
The PCs need to get into a warehouse. Their informant has told them that there's a back door but it's barred from the inside at night so it can't be opened from the outside without some sort of magic. If it comes up the DM reminds the players that knock can heard up to 300 feet away. If someone can get inside they can open the back door. You'd rather not kill any guards if it can at all be avoided.
Casing the place, the PCs notice several things
- There's a single guard but they're sitting about 10 feet away from the front door, sitting on a barrel slumped against the wall. You can't tell if they're awake or not.
- The streets at night are deserted, there are crates and barrels along with a wagon on the street. You might be able to sneak into the front door without being noticed, you can't tell.
- The warehouse also has a cupola on the roof for ventilation, you could probably get in that way if you can get up to the roof. There is a drain pipe for the eves on the side of the warehouse out of sight from the guard that might support someone but you're not certain. In any case it could be difficult climb up.
How would you handle this scenario?