Mundane Urban Oddities in RPG Cities

One of the temptations when making a city for long-term use in an RPG is making it "perfect". I don't mean getting every detail (though that is another temptation) but rather to optimize every aspect of it - awesome public transport, carefully thought out highways, etc.

• Real cities are awfully imperfect. Off the top of my head, here are some issues major cities have had to deal with (with a focus on the cities I'm most familiar with, Boston and New York City).
• In Boston, whenever winds exceeded 45 miles per hour, giant windows would fall off the Hancock tower.
• The London Underground tubes are too small to accommodate air-conditioned trains.
• In New York City, the Second and Third Avenue Elevated lines were torn down in the the 1940s and 1950s in preparation for the 2nd Avenue Subway. Decades later, the very first part of that subway is due to open this year (2016) - a very small part.
• Also in New York City, while subway service along the length of Manhattan island is common, traveling across the island by subway is very difficult.
• In Boston, the two main railroad stations are North Station and South Station. While the T (the Boston subway) stops at both of them, there is no direct route between them.
• After huge cost and time overruns, as the Big Dig neared completion (and large parts of it were open) a tunnel ceiling fell on a car, killing a passenger.
• New York City has an easy to understand grid pattern in most of Manhattan. But south of this grid the street layout gets rather interesting (and in Boston you can forget about a grid).
• In Boston, residents will reserve street parking spots they shoveled out after a snowstorm with a lawn chair. Heaven help you if you take that space.

Some of the things that have evolved in our superhero city of Port Henry:

• Elevated train lines and highways cast shadows on the streets below them.
• Built on land reclaimed from a swamp, street `flooding in rainy weather is a frequent problem.
• Many of the trains, buildings, and roads built in the 1930s are beginning to exhibit problems owing to shoddy construction.

Image credit: WBUR Boston from 4 Things To Know About Space Savers In Boston