I love this one. Back in Chicago, I realized the rate I was getting parking tickets at was about the same as the rate at which I would otherwise pay for street parking. I also learned that if you pay the meter, LAZ Parking takes a huge cut, whereas parking fines go directly to the city so I started incurring parking tickets instead.
Also I learned that Chicago doesn't do anything until your third ticket, so if you're going to leave the city, you can park for free for your last couple of weeks. I guess that one is a little more unethical.