iserith
Magic Wordsmith
I'm especially excited about trying this in conjunction with the forthcoming improvements to Dynamic Lighting/Fog of War on Roll20. If you want the desaturated "where we've been" map view turned on, better designate a mapper!
When does that roll out?
Yes, initially, but I think that's probably just a function of me having less confidence and experience as a DM. Eventually I think it should become more instinctive - knowing roughly how much detail/what sort of hints to describe to characters with differing levels of perception abilities. Right now it takes me a non-trivial amount of time to dream up a secret door + hints that aren't either a) crashingly obvious or b) impossibly obscure. But I figure that will get easier with practice.
The way I handle it is that each PC establishes his or her exploration task upon entering the adventuring location. There's nothing "passive" about that activity - it's something they're doing in an ongoing basis. (Passive checks resolve tasks with uncertain outcomes performed repeatedly.) I make a note of it and the relevant passive score.
When I describe the environment, there's always some kind of clue embedded in the description. It's not "gated" behind a DC and check - this one's a freebie so the players have enough information to act with agency if they're paying attention and engaging in the scene. This means I don't have to think about DCs to get that initial clue or describe it from a particular character's perspective. This may cause the player to choose to do some other task, switching from Keeping Watch to Searching for Secret Doors or Working Together, for example, because something about the description of the environment indicated that would be of benefit.
Whether they describe a task different from the one they did upon entering the adventuring location or not, they get a result for their respective tasks in the particular area being explored. The task the player described is resolved, so the PC finds the trap or the secret door or tracks or whatever without any further hinting. (There's really not much interesting interaction to wring out of continued hinting and back and forth in my view.) What they do with that information may result in further ability checks if the result is uncertain - figuring out how to disarm the trap or open the secret door, etc. Finding the thing is only the beginning of the situation.
As for Investigation, that's a mechanic to resolve the times when the character is trying to make a deduction in my view. He or she has the clues and now it's time to put that together into a theory. It's not a "search check."