I did that for years. Parking at my apartment building was $350/mo (and was valet only, so it was also a major PITA).

I often parked at my work garage and walked home, but many times parked on the street/at meters, and didn't sweat it too much if I got the occasional ticket (not getting back to the car early enough, usually) It was virtually impossible to run up a total anywhere near the cost of the less convenient valet parking.

For the longest time in college, garage parking in Harvard Sq was $14-20/evening and a residential parking violation in a nearby neighborhood was $10 or $15. So we often used the "stochastic parking garage".