That is close to what I was thinking, although I am shifting my thinking a bit. I am now wondering if it might not be better to create a few establishments with a couple of things to do/people to meet in each, maybe in different neighbourhoods. Give each a little flavour so you have enough on an idea in your head to improvise.
I have 3 tavern/inns in my city redux. The largest and best known, the Mountain Bear, is where the military heroes and city guard hang out. Upscale, safe, big, expensive. Another smaller "rival" bar (still uptown) where the ones who are pissed about something that happened in the Mountain Bear go (and also where the serious drinkers hide out to over-indulge after hitting the MB). Finally there's a fisherman's tavern, Cap'n Mooneye's, near the wharves---that's more low-class, but also where the main secret society that are working against the doppleganger King have their headquarters.
I have a list of NPCs from the other parts of the city that visits each. The players go in the first time and not much happens, they get the lay of the land---and I think they aren't paying attention. Maybe they just get a room. Then, at some later time, perhaps after leaving and returning to the city, they suddenly have a reason to talk to one of the NPCs they know hang out in the locale---then they return with purpose and I try my best to make it a bit non-linear...and wish I did more, i.e. has prep'd more twists/turns/non-sequiturs. It's for the later, the non-sequiturs, that I want some better tables.
So they pick the evening they want, go where they want, summarize what they are doing when they get there (no playing out gambling or small talk, just get them to state their actions) and based on where they are and what they do or who they talk to they (a) trigger a meaningful social or combat encounter, which cam be improvised based on what they do and what's going on in the bar, (b) trigger some sort of skill or event check, like for success in gambling or possible encounters for walking home though the bad part of town, which can be improvised using existing skill or random encounter mechanics, or (c) trigger no significant event unless they change the plan for the evening.
The more I see people talking about their ideas for random event tables, the less it seems to me like they would function well in play. Which is why I'm leaning towards The Alexandrian style prepping of situations.
I keep feeling like I am missing something. This is what I'm doing and it works
alright, but also it sounds like you both were struggling with something that I can't put my finger on. Is there something about the modern game that makes this difficult? I remember that happening in another thread---me thinking "what are we talking about" and it ended being something that had come and gone during my D&D cold-sleep. I think it was one of the Alexanderian posts on railroad plots that Beoric or TS said had "changed they way they played" but felt like Mom and Apple Pie talk. This feels like that. I am just not understanding something here, so there are these odd interjections (like the two I just quoted from you both) that give the impression that something was revealed/resolved, but instead I feel like the conversation just spiraled back on itself and we've been all saying exactly the same thing since the very beginning.
Honestly, it sounds like you are all doing this, and then each randomly says
"Eureka! I should start doing this!".
I am terrible confused. Where's TS to grogsplain it all to me?