You can pretty much just replace all instances of "Boston" with "Chicago" for that entire article (except the 2 hour grace period thing).
When I lived in Chicago and had a truck (tiny little Chevy S10), I came to know first hand how aggravating the street cleaning schedule was and built up a collection of tickets to prove it. My truck also got broken into despite it being completely empty and having a bench seat clearly showing anyone who walked by it was empty.
I'll also never forget coming home around 7pm on a weekday night and literally driving all over the neighborhood for 2 hours waiting for a spot to open up.
This is why I was happy they jacked up the parking rates in Chicago - they now roughly match the actual value of the spaces for a given moment in time. I hope they do so in Boston now that I live here (technically Somerville).
> literally driving all over the neighborhood for 2 hours waiting for a spot to open up.
The NY Times in a feature on holiday parking in NYC mentioned this guy's blog which is all about finding a parking space before/after/during street cleaning hours in NYC. I wouldn't think reading about someone finding a parking space would be so fascinating but it is strangely entertaining.
As far as I know, that's originally from Yogi Berra. From wikipedia: "On why he no longer went to Ruggeri's, a St. Louis restaurant: 'Nobody goes there anymore. It's too crowded.'". (http://en.wikipedia.org/wiki/Yogi_Berra)
One of the biggest tricks here is the fact that every town (which you may drive for 10 minutes and pass through 10 of within a few miles) has completely different parking laws.
Brookline you can't park overnight on the street- period. Boston you can park for free overnight at a metered spot as long as you get in it after 6pm (8pm some spots). Some areas an unmarked spot is open for parking (as long as no sign speaks otherwise), other areas you'll likely get ticketed or towed. In Somerville you can park a motorcycle in any 'permit only' spot and its ok (I called 311 and asked), and Cambridge it will land you a $30 ticket to do the same- god knows about Boston.
Street cleaning is a joke and its really just a way to annoy people and raise revenue (which I understand the city needs, but if everyone uses the services- everyone should pay for them. Now if they money goes to only maintaining the roads, that is more understandable).
I agree some some comments that you don't need a car if you live in Boston. Living in Back Bay for 2 years I had no need of a car, but now that I'm in Somerville it is nice to have one.
The rates are a little bit much for some offenses.
It's quite normal to see delivery trucks (FedEx, UPS) with 20 tickets on their windshield. It's just a cost of doing business.
And it's not like the violations are rational. The restrictions are designed to seem reasonable, but really just to snag as many people as possible.
For example there is no overnight parking on the street - at all - in brookline (suburb of boston). And of course the fees are at least 3 times as much as any normal city charges.
I'm so glad I don't live there anymore.
In Pittsburg the law is you can get give someone a parking ticket for street cleaning, unless the street was actually cleaned, AND the car was in the way (so move it before or after and you are OK). Not so in boston - they watch the clock and as soon as the time starts (to the second) they give everyone a ticket. But of course there is no budget for an actual street cleaning truck.
When I lived in Chicago and had a truck (tiny little Chevy S10), I came to know first hand how aggravating the street cleaning schedule was and built up a collection of tickets to prove it. My truck also got broken into despite it being completely empty and having a bench seat clearly showing anyone who walked by it was empty.
I'll also never forget coming home around 7pm on a weekday night and literally driving all over the neighborhood for 2 hours waiting for a spot to open up.
I was so happy when I got rid of that thing.