I'm not going to request multiple stealth checks for attempting a single thing (ie - if you sneak into a camp, that's going to be one stealth check, regardless of the number of sentries) because otherwise you make failure very likely, even with competent PCs.
That said, more complex stealth scenarios are more difficult to adjudicate fairly: you want to stick to one roll, but you also want the PCs to be able to react to things they observe and take more or less risk. I think if you're keen on running an extended stealth scenario and not just have it fail due to lots of rolls, you want to come up with something more complex: the existing rules just suck for that kind of thing.
Wth is a cahoot?
-Brad
A skilled character will always believe he is being stealthy, so the more skilled you are the less likely you know you are being spotted. Very smart players will make a stealth check and then a perception check to perceive if they are detected by someone else. They won't wait to see if the guard reacts, they will try to perceive if they are noticed. TBH I am the only player I know of that does this, but my kids do it now after I explained it to them.
The same skilled PC could also make a stealth or perception check to see how stealthy a none stealth Skilled PC is doing on his stealth check I.e "dude you stand out like you had fairie fire cast on you."
PC unskilled in stealth really wouldn't know if they were being stealthy until they failed. A PC with a high passive perception might be aware at how bad his attempt is.
Using the above a stealthy PC can make his stealth check and then use a perception check to gauge how he is doing, which will allow him to keep the same stealth check and continue or maybe role again if he perceives something is tipping him off. Likewise, a smart enemy might notice the PC but not try to give it away to lure the PC in, the perception check might pick that up.
the more skilled you are the less likely you know you are being spotted.
I would assume that training in stealth would include knowing when you've been spotted.
Does a PC trained in Survival have no idea when he becomes lost? Surely they'd be the first to know.
The only way I can imagine this playing out is if the PC had some kind of Flaw related to overconfidence or Hubris.
I guess it falls into the question of, are you rolling to determine the outcome of a certain activity, or are you rolling to set the difficulty of something else (a DC for guard's perception to beat)?
Right, so, let's discuss this one.
To begin, it seems like players in this game make checks either before, or as part of declaring their actions. In fact, from the language used, there's not a lot of actions being described in-game, but there is a lot of mechanics-speak.
There also seems to be some element of finding a way to re-roll a check you don't like by supposedly perceptioning any errors.
A lot of this is backwards to me. At my table, players don't declare what checks they're making. Instead they describe what they're doing and how they're doing it. Like "I sneak around, sticking to shadows and cover, so that I can get over there without being noticed." At that point, I can call for a Dex (stealth) check, if I need one. I mean maybe that action automatically succeeds. Or automatically fails. But it's up to me as DM to determine that and set a DC. It's not up to the player.
But whatever is going on happens as part of the in-game circumstances. And any dice are tied to efforts in pursuit of a goal (they are not tied to efforts alone or to goals alone). So "I'm sneaking" on its own isn't enough to get a Dex (stealth) check. And "I make a perception check" says literally nothing at all about what you're doing or how.
Interesting to see someone who plays it so thoroughly differently than I do though.
-Brad

(Dungeons & Dragons)
Rulebook featuring "high magic" options, including a host of new spells.