I have done things like this and while I love the freedom of a car, it makes me realize why I don't own on in a city area (NYC). I spent about $350/month in parking, 2 $55 parking tickets, 1 tow $300, and at the time gas was $4.50/gallon. I only needed it 1-2 times a week since the subway is usually faster anyways. Moving the car for alternate side parking or whatever was such a pain.
1 parking ticket was an alternate side street cleaning offense which went into effect at 8am. I parked there from 8:01 to 8:03 and the ticket was written for me at 8:03am.
The other parking ticket and towing was on a street I park every day but 1 day some jerk got a temporary no parking for about 100 feet in front of his house for moving. He posted the signs backwards on some tiny tree so the text WHICH WAS HAND WRITTEN was wrapping around the tree. I never saw this sign (At midnight) and even if I did I couldn't read it. I could have easily fought the ticket and towing costs but taking a day off work to do so was not worth it.
So anyways I have no car. I use Zipcar. They are in toronto too. Check it out.