Thanks so much for the super-thoughtful response!
With regards to interrogation sequences... they only happen because the players make it happen. One time, we saw an NPC buried up into the neck in the dirt with "Oathbreaker" written on his forehead. Instead of having a conversation, it became a whole thing where they immediately bust out the Zone of Truth spell because they were convinced that the few answers he was willing to give weren't truthful (because he didn't know the party / the party didn't establish trust with him and he was afraid of being coup d'etated if he said the wrong thing).
I'm totally going to take your advice into account. I don't have any problems with giving the PCs the information they need to know (or where they need to go to get it), but there seems to be an extreme lack of trust between the PCs and NPCs in many of the games I play in, and I don't really know how to handle that.
Sure, they make interrogations happen, but that's the symptom of the problem, not the problem in and of itself in my view. It seems reasonable to be skeptical of an "Oathbreaker." And if there has been a lot of deception on the part of NPCs in the past, then that's all the more reason to bust out the zone of truth. Mind you, this distrust may even be due to experiences these players have had in other groups under other DMs. So a certain amount of deprogramming may be required and that's going to take time.
Time pressure in particular is part of why I'm really hype to be running Tomb of Annihilation (I'm running that after this -- this is a practice Adventure so I can get my bearings before I go full campaign). I'm going to have to think creatively about how I can change things based on how much time goes by. I'll start doing that today as I finish up my Part One notes.
One thing to consider is how to communicate how things might change if they dilly dally. Foreshadowing and telegraphing are your friends here. Or you can be more direct. What you're essentially giving them are the stakes for their decisions so they can understand the risks. "You CAN long rest more often, but it means X, Y, or Z. Plan accordingly." If they are not aware of the risks beforehand, then it's unlikely they will factor that into their decision-making.
We actually don't spend all that much time in a town (surprisingly!), but most of the stupid things do tend to happen in towns. The Bearded Devil thing actually happened in a dungeon. Obviously, this is going to be really great because the first adventure I'm running is a highly-modified, 5e-converted version of Speaker in Dreams, which takes place almost entirely in a town. I'm hoping that by keeping things fast-paced, or moving people along, I might be able to avoid this. I think you definitely have a point there!
Once thing I've noticed over the years with town-based adventures is there's this thing where almost every minute of the day is played out in a way that doesn't appear to happen in adventures based in other locations. So when the PCs aren't actively engaged in the events of the adventure, it's like "What do you do?" and everyone thinks they have to come up with something to fill the time. This is when you get the shopping scenes, the pickpocketing, the inane NPC interactions that go nowhere, the stabbing of the barkeep and fighting of town guard.
What you can do instead is give each player a set amount of tasks they can perform per adventuring day. These are things they can do when they aren't engaged in the events of the adventure. I recommend 1 to 3, tops. Probably just 1 for your Speaker in Dreams adventure, where 3 might be more appropriate for a full-on city-based campaign. Then think about making a list of tasks someone might do in town - resupply, gather info, work a trade, carouse, etc. Downtime activities are useful for ideas for this. None of those tasks should be anything that derails the adventure or causes pointless trouble, but do offer a benefit that can be used during the adventure (extra gold, contacts, info, etc.). Resolve quickly, maybe with a single die roll and some narration, then right back to the adventure you go.
I have something like this set up in my Sigil-based Planescape game. It's fairly complicated, so I can't share it here, but it is very good at keeping the pace of things moving forward while offering meaningful trade-offs.
Sounds like I'm going to be running with "Roll Insight. Yeah, you really don't think you're getting anything else from this guy."
Some will disagree with me here, but I would caution against telling players what their characters think or calling for ability checks when players have not described wanting to do something that has an uncertain outcome. In the particular example you give, you're basically trying to communicate something to the players about not being able to wring any more information out of the scene, but doing so in the context of the setting while using the mechanics as a form of legitimization. This is dangerous territory in my view, especially if that Insight roll turns out really low. What do you do then? Give the same result and leave the player with a disconnect between what he or she sees on the die and what you're saying? That can lead to further distrust. Better not to paint yourself into the corner with this sort of thing, I say. You can avoid it by just leveling with the players which communicates more clearly, avoids assuming character action, and stops you from telling players what their characters think. This will probably go a lot further toward establishing that trust you want to foster.
I recommend checking out the social interaction rules in the DMG. Therein, it says that the NPC should be given personal characteristics (trait, ideal, bond, flaw). After interacting with the NPC for a time, a player might describing the character as wanting to confirm one of those characteristics (which you should already have been playing up during the conversation). This can be determined with a Wisdom (Insight) check. On a success, you tell the player what the characteristic is. He or she can then play to the characteristic to gain advantage on subsequent checks to influence the NPC's attitude. On failed Insight check, the character can't determine what the characteristic is. This has the effect of giving players specific things on which to base their level of trust of the NPC. Otherwise, it's just whatever the DM says, which may or may not be true. It's much more concrete with these social interaction rules in my experience. It also gives the non-Charisma based characters a pathway to assisting in social interaction challenges by being the Insight guy or gal.
