So I did my homework on urbancrawls. I read the full series by The Alexandrian (which is very good and I would definitely recommend). I read other people's responses to it. I read some of the games and splatbooks he talked about. I've read a lot of Vornheim. I took a gander at Magical Industrial Revolution. Esoteric Enterprises looks promising but I never took the delve. I looked into what various 5E adventure modules offer (spoiler alert: disappointingly little. I really hoped Dragon Heist would have advice or structures but not really). I've relied a lot on Medieval Demographics Made Easy, like most people who've jumped into this rabbit hole. I read about it in all sorts of places, getting a sense for change over time. I've read a good amount of The Time Traveler's Guide to Medieval England. I've pored over tons of maps of medieval cities. I've looked at maps made for RPGs specifically. Both professional ones in WotC books and whatnot plus homemade ones like this.
And the fact is that they are nowhere comparable in size. At all. That wouldn't bother most gamers of course. Several of these are explicitly meant for noir stories about sprawling labyrinthine dreamlike cities like Los Angeles or Victorian London or Ankh-Morpork. It's fantasy, after all. But I'm also positive that a lot of them weren't meant for that, and that instead the reason why most of these maps and urbancrawl procedures were made this way is because their creators didn't really care to do any research and just assumed that their scale was realistic. Which is fine. Again, they want to have their adventures take place in gargantuan cities. But I was just kind of shocked that I never found a single instance of someone who was satisfied with or even actively seeking a more realistic scale for the medieval period.
I was really hoping the cities in Skyrim and Oblivion might be accurate after doing all my research since I knew they were really small. But a few calculations later and I realized even those towns are absurdly undersized, so they aren't that helpful either.
One of the coolest things I found was this website which is a pain in the ass to use at first but when you clear all the shit off the screen you can overlay a map of medieval London over modern London and adjust its opacity and compare them. It gives a great idea of what a medieval urban layout is like. But even medieval London is uncharacteristically large for the period.
I try to mostly use the 13th century as my point of reference. I've heard it said before that a good rule of thumb is 1 sq. mile per 50,000 people, but... for anything smaller than the very largest handful of cities on the entire European continent, that's just not useful at all. 90% of the settlements in my setting aren't even close to 50,000 people.
One of my weird needs that I don't see echoed across other people working on this is that I only want, like, a bit of material for urbancrawling. I don't want to run a whole urban campaign, but I also want something more for my players when they go into town. Like, the normal thing for the stuff that happens between hexcrawl/dungeoncrawl adventures is for you to say, "welcome to the capital! Here's the part of the map you go to for safe resting and to store your treasure. Here's a list of items you can buy while you're there." And then if there's something specific you need like to go to the temple or cartographer or something then the DM just takes you there in a pretty ad-hoc fashion. I just want something slightly more in-depth there. It's kind of why I actually prefer the small, realistic sizes. The amazing, sprawling, urban landscape most of these systems and resources aim for is too much for what I need out of a city. I also want a model that will scale well with towns and villages, too. Arguably even hamlets.
And I really want whatever kind of gameplay I run for raiding and conquering a settlement to allow for the raiders to actually fight and navigate on the ground level but make progress in increments measured by the neighborhoods themselves. See, I've explored the idea of ignoring scale and reducing each neighborhood to some abstract mechanics. So that the act of breaking through the southern wall and overwhelming the forces in the merchant quarter can be done just through, like, dice rolls and charts and whatnot. But my knowledge nags at me. The knowledge that the whole place is so small that it would take, like, 2 or 3 or maybe 4 movement actions to even get from one neighborhood to another, and that an abstract system is inevitably going to clash with a player who says, "wait, if we have to abandon the southern wall because of their bone devil... how about I just head back to the town library and grab the binding spellbook I saw yesterday?" The DM who decided they didn't need a map and could abstract all of this and has been taking all their advice from a baseline assumption of Los Angeles-sized noir city tropes... that DM wouldn't know the right way for this to go. They don't have a great sense for how long that would take. They probably would assume it isn't viable but, in a medieval European city, it might actually just take 4 or 5 rounds of combat to get there and back.
Medieval cities are frustratingly close to dungeons in size, but that scaling is also too small for most of them. Like, I'd almost want to run a city like a dungeon but then it would be a huge dungeon. Let me get into some numbers and units. Don't worry, it'll be helpful.
Furlongs are a good medieval unit that gets used in everyday life. 1 Furlong is 1/8 of a mile (660 feet). So if you had a dungeon map with 5 ft. squares, that would be 132 squares across (for 10 ft. squares, 66 squares across, of course). That's a pretty chunky dungeon. BUT... it takes about 5 minutes to walk the distance of 2 Furlongs. And that's just walking, not even running. That eats up, like, no time at all. And most medieval settlements are only a few furlongs across, if even. One square furlong of land in a settled area could be the home of, like, 200 people. Or a lot more if it's in an urban area, which is way more dense. Why do these distances matter? Because it's fucking hard to track the amount of time consumed for each thing the players do in the city. And oftentimes, they wanna stop into town, do a bunch of shit, then go back out and adventure more. And I don't know if that'll take them less than an hour or more than a day.
My first ever job was being a legal courier, which is more often just called a "runner." I literally ran errands for a couple of law firms, on foot. Most lawyers have several bank accounts, handle everything in checks or cash, own some property, and of course have stuff to send to/pick up from the courthouse every single day. The distance between where I started my shift to its furthest point away was about 2100 ft., but I hit around 8 stops along the way. That would be a 10 minute walk without the stops, but instead it usually took me 1 hour to do everything. Most of the time you spend in urbancrawl adventuring is really the time spent inside the buildings, whatever it is you're doing at each stop. But that shit's kinda hard to figure out without getting annoyingly granular. I don't know how long I spent in line at each bank, or how many seconds I would be waiting for the bank tellers to complete my deposits, or how long it took to get through security at the courthouse. I just know that a lot of really tiny, almost meaningless activities that most DMs could easily justify handwaving ended up eating a non-negligible amount of time.
This is the kind of shit that makes me wish I played storygames sometimes. I kinda lied before. There was one WotC adventure that actually had advice for urbancrawling, and it was the 5E starter kit's Lost Mines of Phandelver. In the second part of the adventure, which you spend in the town of Phandalin meeting it's inhabitants and inevitably getting caught up in their little drama, the text advises the DM to not get bogged down in the specifics, but to instead imagine they're the director of a movie set in the Old West. You know, just kinda going from one scene to the next with each location having one major development happen, all at the pace of drama. And at some point, introduce X plot development when it seems appropriate, just kind of "in between locations." The sun goes down when it would be dramatically appropriate, you know? And the players aren't going to have anything else going on anyway, so go ahead and lead them along your rails as you please. It works really well for that adventure, but again, not great for my knaves who keep coming and going from town on their own timetable. I could just choose an arbitrary unit of time, like, "you can do one major thing every 15-minute urbancrawl turn" or whatever. I don't know. It's not a system with the kind of mechanical verisimilitude that might be helpful if they, say, break out into a chase scene or are, like, rushing to the castle to stop an imminent evil ritual right after finding out about it in a plot twist that happened at the tavern. And again, how do you define "major?" I know from firsthand experience that you can hit a lot of stops in an hour. But hitting a delay at just one of them, like a really long line or something, could cost me an extra 40+ minutes out of nowhere.
I'm sure eventually I'll come up with something that satisfies me and isn't useful for anyone else. This is a classic example of my DM brain getting bogged down overthinking something theoretical that wouldn't be of much consequence in actual play. Except I keep having issues with it in actual play so maybe this is worth resolving?? And I know for a fact that WotC thinks it's worth considering because in 5E D&D, the special ability of the Urchin background is that you can travel twice as fast within a city as normal. Look how much of a goddamn headache it is to make that ability meaningfully useful. Ideally, I would love a really elegant solution that has the mechanical flexibility to satisfy investigation gameplay, carousing gameplay, pillaging combat, chase scenes, spreading fires, spreading plague, and so on with all the same framework instead of having a separate way of resolving each of those. A miniature urban hexcrawl or something seems like it could solve sooooo much if done right. I'm sure the Alexandrian is satisfied with his solution but, again, it doesn't help me for my adventures that only occasionally require activity in cities, but during which the amount of time consumed and layout of the place seems to keep coming up.