I worked at the college radio station located in the on campus student center, which also had a hotel attached. It was, like all campuses, annoying to find parking / work out transportation.
Then one day I just needed to run get something, so I parked in the hotel loading zone. I ran into someone and chatted for about close to an hour and then, remembering where I parked, freaked out and ran outside.
Car was still there, no problems.
In true hacker fashion, I went and sat in the car and waited to see when someone would a campus metermaid would come along.
They never did!
And so for the next 2 years I parked there every day.
In the end I did receive 6 $25 tickets and, ingloriously, I was towed once which cost me $250.
Compared to a parking pass it was an absolute steal, and in true "things you're allowed to do" form, it helped me realize the risks of transgression are lower than you think.