The Attentioncrawl and Citizen Playbooks
I was listening to the Dead Letters episode on Magical Industrial Revolution, and they were talking about the difficulties of representing cities in tabletop roleplaying games due to their sheer physical size and density. One difficulty that they did not address is that in a dungeoncrawl, hexcrawl, or pointcrawl, each "node" is connected to a finite number of other nodes, and those connections are obvious once discovered. In a citycrawl, this is not the case: if the city is unmapped, PCs have no leads on where to go except general ideas of what can be found in a city (a blacksmith, an inn, a temple, etc.) or places and people specifically mentioned by inhabitants of the city (Grazzo the bartender mentions a shipwright who works in the docks owes him money). On the other hand, if the entire city is already mapped, there are a large (possibly overwhelming) number of places for PCs to explore, much of it repetitive (in a large city, there could be dozens of blacksmiths, inns, or temples).
I think of this structure as an "attentioncrawl," because it is heavily restricted by the PCs' knowledge of what exists in the city or their ability to pick one out of many similar options. This is because we are trying to simulate the experience of exploring a city over the course of days, weeks, months, or years in a medium where three hours once a week is a substantial investment of real-time.
The closest analog to living in a medieval city I have experienced is getting to know a college campus. In four years of undergrad, I certainly gained a progressively greater understanding of my campus's layout and how to navigate to where I needed to be. But at the same time, I never entered many of the buildings on campus because they simply weren't relevant to my needs or interests. I think a good system for simulating a city would capture both the way that we learn about cities as we live in them and the fact that different kinds of people have different ways of relating to a city.
One way to accomplish this mechanically might be a kind of "Citizen Playbook"1 incorporating elements of PbtA playbooks and the Loresheet mechanic from VtM v5.
PbtA playbooks need no introduction from me, but the important thing about them is that while different types of characters use different playbooks, even two characters with the same playbook might turn out very distinctly based on which abilities a player chooses.
Loresheets are an interesting innovation of Vampire: The Masquerade 5. They are mechanical advantages that give PCs a specific connection to the broader lore of the game, allowing players to pick and choose what relationship they want their characters to have with the metaplot.
If I were to start designing Citizen Playbooks, I would make a bunch of tiny PbtA-style (or if I'm feeling feisty, BoB-style) playbooks governing different neighborhoods and classes of people (beggars, religious officials, magic-users, public servants, etc.) While any investment in a given playbook would give generic advantages (less likely to get lost in a neighborhood, say, or making it easier to avoid random encounters), each playbook would also contain specific characters and locations the PC would be familiar with and mechanical rewards for having invested in that playbook (i.e. a high rank in the Market Square playbook means a PC can always win chases through the crowded merchant stalls). These abilities would also carry information about the city, so if you have an upgrade in the Docks playbook that means Slippery Pete owes you a favor, you know Slippery Pete is someone you can reliably contact in the Docks.
I think that this approach of mechanizing and decentralizing information creates a much more interesting and engaging experience, since players are now approaching this material through a lens of "how can I interact with X?" rather than just receiving dry exposition about it. Furthermore, the fact that players can choose to only look through the playbooks that interest them means that each player's understanding and way of relating to the city will be slightly different.
Footnotes
As in "city-dweller," not "legally-privileged resident."↩