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A key difference to our approaches is that what you know determines whether or not the players do an insight check.
Not sure what you mean by "do an Insight check".
A) If you mean the players state they want to use Insight ("Can I roll Insight?" "And me, too?"), then here I'm totally with [MENTION=97077]iserith[/MENTION]: the players should state what they do and the DM will determine if an Insight check is called for.
B) If what you mean is that the DM calls for an Insight check, then I don't think I'm changing much. If the players say, "I'd like to look at her body language and listen carefully to her words and see if I can get any clues as to whether she's being truthful" then I can either ask for an Insight check, or just decide to give them the clue, and say, "Well, all she's said is that she hasn't seen him, not that she hasn't heard from him, or tried to contact him..." and see if they take the bait.
As far as the players are concerned the letter could have been a forgery. Or maybe she did write the letter but ensured it would never be delivered and she's just covering her tracks.
To be clear - I have back-and-forth conversations with NPCs all the time. But in this scenario you aren't resolving a contest so the players now know she's telling the truth, at least about the direct answers she's given.
Sure. But as I've said before in many cases (including this one) I think games are more dramatic and immersive (in the sense that you feel what your character is feeling) if you never know with certainty if somebody is lying.
So to me, the specific scenario doesn't matter. If the players think the PCs would suspect the NPC is lying, then the PCs suspect the NPC is lying. The logical result of that would be to try to determine if the NPC is lying: an insight check.
Agreed. I just don't think the result should be black & white. (Note that even if you parse the description of Insight the way Hussar does, it most definitely does not say you should get clear, unambiguous answers.)
So a specific scenario? Like the one I gave earlier. The PCs are searching the house of Baron Von Uppity-Up who they suspect is really The Black Snake. Mr Snake has a reputation of being paranoid, and is someone likely to booby-trap their house.
The group has no idea what specifically is trapped or how. If anything is trapped. What does that session look like in your game?
Ok, you got me. By a "specific scenario" I meant one trap (or one lie). For the occasional trap I can make it a puzzle to solve instead of a straight dice roll.
My answer here is that I would just never run an adventure like this. (At least, I would never write an adventure like this. If somebody like [MENTION=97077]iserith[/MENTION] or [MENTION=6776133]Bawylie[/MENTION] wrote it I would definitely take a look.) D&D just isn't suited for interesting resolution of traps.
And, as a player, if were in this adventure and it was literally just Investigation roll followed by Thieves' Tools roll, I would be bored stiff. Either that or I would play something with high survivability and then storm through the house kicking open all the doors and smashing all the chests, and hope for the best.