Perhaps an entire town that have fallen in love with corruption and injustice, so naturally the rich are in power and whatever they say goes with greedy pawns to do their bidding in hopes of reward or because they are being blackmailed. The gap between the poor and rich is wide here and violence comes quickly and senselessly.
Could be interesting to enter such a city and have several hours of questing to chose who to turn the tables on and change who is in control. To chose to lead a rebellion or leave things the way they are... after all if your character doesn't rock the boat there should be some good money to be made by becoming part of the system. Maybe you can lead yourself to become in power and have a nice flow of materials, ore, alchemy ingredients, and money at the expense of oppressing and inflicting suffering on the towns inhabitants and becoming more of an outcast through the rest of Skyrim?
Just some thoughts..