It's a Group Effort: Resolving Mass Rolls

[Quertus]

They managed to sneak five armies onto the beaches of Normandy did they not? Stealth is a bit more than darting across an alleyway without a guard noticing you. Or you could say I see stealth as quite a bit more than "move silently". Not that I would consider Operation Overlord a stealth check (followed by some combat) but general principles of misdirection and finding places where people aren't watching as closely can be applied on behalf of those who don't know how to work them. ... I'm not really sure why I am going on about this but people seem to have a narrow view of the subject. Also one that often makes it less fun to play.

Player skills vs character skills, maybe?

I don't generally want a "come up with a good plan for me" skill on my character sheet. I expect my rolls to be at the level that I can't - or wouldn't enjoy - interact(ing) with the fiction.

If I'm bluffing my way onto the beaches of Normandy, I want that to be one bluff roll... or a fun minigame.

If I'm sneaking into a crime boss's office, I want that to be one Larceny roll... or a fun minigame.

Now, that fun minigame might well involve (edit: me explaining my plan, followed by) a number of opposed stealth vs perception rolls, and, personally, I'm fine with the notion that, when I plan foolishly enough that I encounter 20 guards, it's a foregone conclusion that it's not if, but when, someone notices me. In my mind, that's bloody brilliant!