So here's an idea for generating a playable urban area in an hour or so. I have written it in white because it has some spoilers for our upcoming game in it and I don't want my players reading it. So players, go elsewhere. It may spoil the fun of getting to figure some stuff out...
Everybody else just use your mouse to highlight the text to read it, or hit the green "print friendly" button at the bottom--that'll give you a black-on-white version.
This method is best for weird/fantastic/evil/stylized cities with some sort of adventurey thing about them. City of Madness, City of Sorrow, City of Angels, et cetera. Cities that are kinda like dungeons. It could work well for the kind of stuff that's in D3: Vault of the Drow* and I1: Dwellers Forbidden City or China Mieville's The Scar...
Anyway, what you do is get yourself a pack of tarot cards, shuffle them, and randomly lay them out next to each other, edge-to-edge in roughly the shape of your city--then take a picture of it. Or you can do it all virtually by just googling up a whole deck of cards and cutting and pasting them around until you've got a semi-continuous shape.
So now you have picture of a bunch of cards on the ground. Each card represents a building or city block or neighborhood--which exactly is not that important for this method. The cards are a map.
Now interpret your "map" as follows:
-Coins/pentacles represent merchants and commercial establishments/neighborhoods
-Cups represent taverns and inns
-Swords represent (in a fortified city) military installations or guard towers, or (in a less bellicose city) ordinary areas where the key encounter will be with guards/soldiers/fighters. etc.
-Wands represent whatever kind of people or establishments are especially characteristic of the city. Like the one my PCs are in now is full of scholars and philosophers so that's wands.
The number on each card represents the status/level/priceyness of the establishment or encounter area and can (optionally) also be taken as, literally, the number of buildings in the cluster. So 9 of coins would be a fancy shop or 9 fancy shops or a cluster of 9 buildings with a fancy shop in it or an area of 9 buildings where there's an encounter with a high-level merchant, etc. Decide how you want to do these things when you start based on your idea of how big the city is.
Pages represent petty bureaucrats with dominion over the thing represented by their suit--commerce, food and drink, military/police/militia, and The City Specialty.
Knights represent knights or other high level fighters in the service of a faction that controls or is very important in that business in the city.
Kings and Queens represent the most important male and female people in each profession and/or the male and female heads of factions that dominate that business in the city.
Now that's the minor arcana. Here are the easiest of the Major Arcana to interpret:
-The Fool is the court jester or just an important entertainer, or maybe even just a big theater
-The Magician is, duh, the local crazy wizard
-The High Priestess is either the highest ranking female cleric in town or the church she is affiliated with
-The Hierophant is the highest ranking male cleric in town or the church he's affiliated with
-The Empress is the most politically powerful female
-The Emperor is the most politically powerful male
-Justice is where the court of law is
-The Wheel of Fortune is where the crazy gypsy lady or other local oracle is.
-The Hanged Man is where they execute or, alternately, torture people
-Death is where you have your graveyard and/or epidermally-challenged adversaries
-The Devil is where the most fearsome local demon or other villain is
The advantage of this system over the usual random city generator and even other tarot-card based location generators is all you have to do is remember what the suits stand for and you've got a whole city or city-like socio-architectural entity in less than a minute with 4 factions, a social hierarchy and a functioning infrastucture. If you use this method to generate a city you will not even need to look at this blog post to figure out what's what. because, of course, the pictures on tarot cards are already based on a fantastic-medieval social structure.
Once you've laid out your cards, take a look at what the city looks like--is the Queen of Cups next to the King of Wands? What's going on there? Is the 10 of cups surrounded by cheap merchants? What's up with that? Figure some things out about this place.
If you stopped there and just did the Minor Arcana and those 11 Major Arcana that you can probably interpret without referencing this blog post, then you'd have made a city with almost no work, which is neat. So if you want to do this shit fast with almost no thought, you don't even need the remaining 11 cards and might want to just leave them out of the deck entirely.
However, if you have some time to think, here are the others, and some associated ideas:
Someone here will fall in love with a PC, or be desirable to them, or maybe it's a whorehouse...
An engine of war? A coliseum? Also, the card has a couple sphinxes on it, so there you go...
A monastery or someone unobtrusive who is secretly someone else.
A big monster. Perhaps chained up in someone's basement.
Some force which moderates the overall tone of the city. Maybe a dissenting voice? Like in the Vault of the Drow this might be the headquarters of the Hey Guys Let's Not Destroy All The Surface-Worlders League.
Local mysterious architectural feature. Perhaps a literal tower. Maybe an entrance to a megadungeon...
Unobtrusive but vastly important place/NPC/mcguffin.
Lunatics? Or one of these guys.
Friendly or helpful NPC.
Someone out for revenge on the PCs because of their actions in a previous adventure. Or, if The Hanged Man is a secret place of torture, Judgment could be the public execution grounds.
Something here explains what's going on locally. Maybe there's a big map or just some talkative people, but this is where you put your not-in-this-city adventure hooks.
*Found out last night Satine used to be able to speak Drow. She learned it off the internet back in the day. No shit. Loser. Just kidding Satine you know I love you. Hey, why are you reading this?