Thinking about cities and their absurd rules, I am reminded of a nickname for Industrial Revolution-era London: The Great Wen.
A wen is a cyst, a tumor. The expression was used to mean that the city's growth was unforeseeable, unruly and out of control (as well as ugly, of course). There's a tabletop game, Itras By, which is all about a city with surrealist inspirations, and one of the many interesting tidbits in the 400-page-long book is about "structural cancer": walls and windows and alleys appearing where there should be none, like an illness of the city.
I'd like to see a game focused on these concepts.