OK. The light is beginning to dawn on me.
You want something in between (a) total table abstraction, and (b) minute skill-checks or awkward conversions. Right?
This makes sense to me---although honestly I've never had this be an issue because I lack the tables for (a), and I don't let conversations get awkward or too fiddly (and I there is no 1e conversational skill checks, except a reaction role...which I often forget to use).
However, there is TONS of NPC conversation---but usually only on-topic based on player agenda.
Here's some examples (although this would never happen with my group).
PLAYER: I go up to the bar maid and proposition her.
DM: She's not interested.
See, we've abstracted the uncomfortable parts away.
Here's something that did just happen with my players that goes a bit deeper:
PLAYER 1 (disguised as Prince Lars): I look for a back door to the kitchen.
DM (me): There's one open on the north side of the Inn.
P1: I walk in.
DM: The owner's sister-in-law is there. She asks if she can be of service.
P1: I tell her I want a chunk of raw meat.
DM (not doing a girl's voice to the best of my knowledge): "My lord? Wouldn't you rather I prepare you one of our finest steaks?"
P1: "No. I..errr...need it to maintain my amazing constitution." (a silly and needless lie)
DM (as cook): "A piece of raw meat? That's...unusual?"
P1: "I have a piece every day---but I wouldn't recommend you do it. You'd get sick."
DM (as cook): "Um. Maybe I should go get Gordy...I'm not sure I understand."
P1: "No! I mean...don't bother him...he's very busy."
DM (as cook): "My lord! Forgive me! I am not used to speaking with royalty! I fear I've offended you!". She knees in front of you.
...(etc.)
The point of all the back-and-forth in this example is the seamless transition between abstracted actions (She asks if she can be of service.) to actually verbal repartee when I (as DM) see an opening to twart/trip-up the player's intent---to add a small challenge to a simple abstracted act.
In this example, the player wants something (raw meat to give to a giant owl), and rather than just make it abstracted/easy on them ("OK. You go to the kitchen and get some".) I use knowledge of the NPC's I've populated the Roadhouse Inn with (e.g. the owner's sister-in-law who runs the kitchen and comes from a near-by farm) to try and add some complexity/challenge to the scenario. All this is complicated by the fact that the PC is masquerading as the crowned Prince is afraid of exposure by acting too suspiciously. When the whole situation starts to spiral out of control in a Marx Brothers-esque manner, that's when everyone at the gaming table has a good time (self included) and even players who aren't technically "present" in the conversation start chiming in on what to say and do.
One other "favorite" lines of NPC interactions include giving instructions to well-meaning-but-seriously-dense NPCs a la the castle guards in Python's Holy Grail. Again: my players want something and I decide it's an opportunity to make it slightly difficult. Challenge is at the heart of any game.
To me, this is a combination of two things:
(a) a well prepared "setting" (i.e. know your cast of actors and the environment)
(b) DM comfort-level with improvisational banter
The whole "plot" is something much larger in the campaign, e.g. we are heading out tomorrow to scout the road north to get to the Steadying.
Also note, I never made a roll. I would/could if I was uncertain of how the NPC would react and I didn't want to "rig" the result...but otherwise, I use my judgement based on my (pre)imagined backstory for the NPC.
This is typical of our civilized/city-stuff: 99% reactive to player-driven motives. In this case, the one player wanted to befriend a giant owl (familiar) of a dead wizard. That's not something I prepped...not a plot-line I put out there for "Tonight's Game"...instead it was just a small tertiary detail of the setting I sketched out almost 6 years ago that the party we just now fiddling with
on their 5th visit to that particular podunk establishment.
You see, that's why I think prep (adding interesting, open-ended, and tertiary details) is
so important---even if the players walk right past them. Those elements give depth to the world, and allow you to do improv that is not linear/obvious/predictable or arbitrary, but instead riffing off of a foundation that persists whether-or-not the players ever discover it. I'm not sure why this matters to me so much---
but it does.
OK. I'm at the end of another long post where I've explained how
I'm doing it...and inadvertently sounding like a lecture. That's a false impression. Our "system" works well enough in that I eventually have to coax the party to get moving because they want to repartee endlessly with NPCs and see what verbal hi-jinx result. This is fun, but not our best D&D. Also, as I mentioned before, it's TOO reactive. They get thwarted a bit by my homespun D&D approach, but it lacks the dynamic injection of (as John Lennon famously said)
"[D&D] is what happens to you while you're making other plans."
So what I am VERY interested in others sharing (in the concrete) how they run City adventures, as I want "something more" to add to the approach I've already been using.
But I don't want a complex web of tables that just ultimately delivers content I'm going to have to "heavily improvise" anyway---because I feel like I've already got that base covered in a way I am far more comfortable with and I think is a step above either (a) pure randomness and/or (b) pure DM-fiat.
Long post. I know. Sorry. But I'm waiting for some work to get completed...
but it definitely serves to clear up what you have been talking about.