Ovinomancer
No flips for you!
This is informative. The sneaking doesn't seem to be useful in your adjudication for avoiding encounters outright, but only for positioning when encounters occur. Do you see any use for a check to see if encounters don't happen at all?If I could add a few details to your example, (a) the DM tells the players about some circumstances that will make sneaking easier if they work together, so (b) the players declare actions to coordinate their attempts at sneaking, resulting in (c) the DM calling for a group Stealth check to see if they all succeed or fail as a group. Honestly, I still feel like I would need more details to understand what about (b) leads to (c) rather than to separate checks to determine whether each party member is noticed individually.
Since it doesn’t matter how I would adjudicate in the above example, allow me to explain the typical circumstances in which a Stealth check is called for in one of my games to shed some light on why I rule the way I’ve stated. (1) The DM describes the environment and any available options for interacting with it. (2) The players declare that their characters are traveling slowly in a certain direction, sneaking in order to avoid the notice of any creatures they might encounter. (3) The DM calls for a Dex (Stealth) check from each player to individually determine whether each PC remains unnoticed in case of an encounter.
EG, in the overland travel rules of the game, the party can elect to travel at a slow pace so that they don't suffer disadvantage for travelling stealthily. When this happens, is there a check to see if no encounter happens because of the sneaking, or are you enforcing planned encounters and using the stealthy travel as an input to determine positioning in those encounters? I very much allow for the former -- I wouldn't use a group check to determine positioning in an encounter, but whether one was warranted at all.