Lyxen
Great Old One
You appear to be double dipping on the surprise factor, though. Assuming the threat is quite real and these hidden monsters are going to attack, you seem to advocate for giving the party a "group check" first to notice the monsters (with some PCs excluded from said check for doing other things/not being in front rank/whatever DM whim), and then you want to give an individual surprise check to every PC as combat begins. I (and it seems many others commenting on the lengthy exchange here) would not do that as a DM. What you are calling a "group check" is really not. It is each PC making a Passive Wisdom (Perception) check, as they are allowed, to avoid surprise. Some of them might be auto-failing. Combat then begins accordingly.
OK, I think we are progressing, let me try to clarify:
- My main goal here is to allow a party which is well organised a chance to actually notice threats in advance and react accordingly. Saying "you are ambushed" whatever the PCs did to avoid this seems to be severely ignoring the declaration of the PCs (I don't want to go into the player agency topic, as it's often overblown, but it's really the idea). So opening straight up with "you are ambushed" when not only is it logical, if you take the appropriate precautions, to have a chance to notice a threat, but there is a full support from the travelling rules there.
- As for the "double dipping", although it might seem that way, practically, it will not happen, let me explain why below.
But before going into the two possibilities, please remember that, in actuality, not all the people in the party will use their PP to notice hidden threats, only those actually watching for them, for once, and the marching order recommendation might even winnow that further, so it's not like everyone in the party will already have their PP taken into account, it's probably only a minority unless the party is in what they think a very dangerous area and have everyone looking for threats.
Now, about the two possibilities:
- If the party notices the hidden threat in advance, there will not be surprise at the start of the fight (assuming that there is one, the PCs might decide to avoid it), since the party will be aware of the threat. And note that it works perfectly RAW, the monsters' stealth checks will have been negated by their discovery ("Until you are discovered or you stop hiding, that check’s total is contested... etc.") so they will not, for the intent of the surprise rules, "be stealthy". So no double dipping here.
- If the party does NOT notice the hidden threat, the ambush will play out as normal. But this means that the characters watching for a hidden threat have ALREADY had their PP overcome by the stealth check of the ambushers, so any new PP check (which might be "double dipping" if you want) does not give them an additional chance. The PP is fixed, the stealth check has already been rolled and is still valid, so these characters who were watching for a hidden threat will be surprised (which is only normal, since they failed to notice it before anyway).
HOWEVER, there remains the case of the characters that were not specifically looking for a hidden threat in advance, either because they were at a bad position in the party or because they were doing other activities while travelling. Although the PP of these characters was NOT counted for the group's chance of success (as per the travelling rules), there is NO REASON for them not to have their surprise check.
In all probability, they will fail as well, since they were not lookouts and their PP is probably lower than the people who were on the lookout. But they might succeed, and that is absolutely normal, at the last second, to register something or have an instinctual reaction, for a hero such as they are. And that's what I don't want to obliterate I don't want to autofail them at that stage, it's not fair and not supported by the rules. Note that if they react, at that stage, it will affect only themselves, not the others.
And again, if the DM wants to autofail them or give them disadvantage for being distracted, he can always do whatever he wants. But for me, it's not what the rules say, and it's also not only not fair to the character, but also very discouraging to take up interesting tasks like mapping or foraging.
Anyway, as you can see, it's completely aligned with all aspects of the RAW, very logical, but also supportive of intelligent play, where characters make choices and take decisions, while at the same time not spelling out a death sentence either, these are heroes after all.