We very intentionally in 5th edition put stealth in the domain of the DM...This is actually a rare case, in a rule, where we right up front in the hiding rule in the Player's Handbook, which is in the chapter called Using Ability Scores, we tell you the DM decides when circumstances are appropriate for hiding. The reason why we pointed that out is we've tried, in the previous edition for example, a more mechanized approach to stealth where we provided a very clear cut set of circumstances in which you could hide.
The thing is, that works when you're dealing primarily with stealth within combat, but because so much of D&D happens outside of combat...you're eves dropping, you're trying to avoid notice in a crowd, you're trying to escape a dangerous situation and avoid notice...And there are a lot of environmental factors that can come into play, the quality of light, how noisy a place is, are there things to hide behind, how attentive are your potential observers, so many factors.
We decided this is where we just need to, right up front, acknowledge this, more than almost any other part of the game, is going to rely on the Dungeon Master, the person who runs the environment and all potential observers, rely on the DM to make some judgement calls.
Which can mean there are cases where the DM might decide that no rolls are even necessary. Because a group might say we're going to dash out of the Duke's grand ball avoiding notice, and the DM might decide that well the dancing troop in the ball, because they just accidentally set the curtains on fire and there are people screaming and running in the grand hall, they're not even paying attention
...This is an area where we wanted to make it doubly clear that really really really the DM is going to be the referee on how this works...it's always true that the DM is the final arbiter at a particular table. But more than ever it has to be true of stealth and here's why. Often when you're sneaking around and when your foes are sneaking around, there is hidden information. You, as players, don't know everything. Because that's why we're even talking about stealth; if someone else is sneaking up on you, you don't know it, you don't have all the information. And so the DM, this is an area where the DM has to hold their cards a little closer to their chest than they do normally with certain things in the game. Because otherwise you can have situations where all the drama is lost because well it's obvious that this sneaky situation is happening.