As a South Side resident, I have seen residents and visitors park in extremely questionable spots. The South Side does not have a parking problem; it has an enforcement consistency problem.
Residents say they are getting ticketed in or towed from spots they have been using for years. In that case, they should have been ticketed or towed years ago -- action that would not have reinforced the idea that these spots were legal.
Too often, cars park and get towed in a never-ending cycle. These spots eventually become risk-free once the towing or ticketing ceases in the evening. There needs to be consistent towing/ticketing or a sign needs to be placed indicating the legal parking zone.
Consistency is the issue here. Tolerating illegal parking Sunday through Thursday (evidenced in the lack of or reduction in ticketing/towing) reinforces the idea that these spaces are legal. I am not saying the answer is a constant seven-day towing blitz, but rather it is better signage to indicate at what point a car will be towed along with more consistency in enforcement. Ambiguity allows for unique interpretations of what a legal parking spot is. I suggest we work to clear up this ambiguity and get proper signage.
Parking laws are rules that apply to everyone, without regard to residency. We can either fight to change who the laws should apply to (we won't win), we can complain (we won't change anything) or we can work to make this a better situation moving forward by demanding less ambiguity and more consistency.