I'm going to throw
Milwaukee into the mix. While driving in the city is a breeze, the parking situation is absolutely insane. I can't find the source right now, but about 3 years ago there was an article on the situation showing that Milwaukee writes more parking tickets every month then NYC does in a year. They've got it down to a science that produces $25 million in revenue for the city annually. Living there, you learn to expect a ticket on your car at LEAST once per month...and that's if you know all of the rules.
Milwaukee has a fleet of 10,000 parking checker jeeps. They are constantly on the streets looking for people to write tickets for. You can't be parked illegally anywhere in the city for 10 minutes without getting a ticket. In addition, you need to obtain parking permission to park on any city street overnight. If you fail to request permission before 10pm, you get a ticket. If you get permission but fail to follow all of the parking rules, you get a ticket. If you don't know about the rules (which is likely if you're a visitor because they're only posted ONCE at the border of the city on every street), you get a ticket. You're only allowed to request permission for the same vehicle in the same block three times in a month. If you have a guest in town for longer, they need buy a $20 (4 month) Parking Permit. Even if you have a permit, and you somehow don't follow the proper overnight rules, you get a ticket. It's impossible to NOT get a ticket in Milwaukee.
Check out the regulations for overnight parking here:
Parking Regulations
Here are some highlights:
There is no parking on city streets between 2:00 a.m. and 6:00 a.m. Monday through Saturday unless the vehicle displays a valid night parking permit or has night parking permission.
On even-numbered calendar days (before midnight) a vehicle with a valid night permit must be legally parked on the side of the street with even house numbers; on odd-numbered calendar days (before midnight) a vehicle must be parked on the side of the street with odd house numbers. The even or odd date will be the date three hours before the 2:00 a.m. no parking without permit goes into effect.
If a snow emergency has been declared, night parking regulations are in effect from 11:00 P.M. to 6:00 A.M. on all city streets regardless of the winter parking regulation.
No overnight parking is allowed on through highways and mass transit (bus) routes from December 1 to March 1. These streets are not posted. For a list of these streets please go to the Winter Parking Regulations page. In case of a "Snow Emergency" prior to December 1 or after March 1, vehicles must be moved to a side street and must be legally parked in conformity with all other regulations on the proper side of the street.
All vehicles must be moved once every 24 hours regardless of permit or permission status.
In addition, parking checkers are on commission and have quotas, so they're constantly out with tape measures making sure you're more than 4' from a crosswalk, more than 12" from the next car, less than 12" from the curb, etc.
I've spent plenty of time in Chicago and parking overnight there is simple compared to Milwaukee.
Milwaukee Parking Regulations: Quicksand for the Unwary Citizen - Milwaukee Commuter | Examiner.com
Parking quota drives ticket writing frenzy, error rate - TODAY'S TMJ4