Startup #5: Map out areas of free parking in major US cities

To my knowledge this doesn't exist yet, and if it does, using it would have saved me a lot of parking ticket money. From living in Boston for 5+ years, I've found that there are thousands of little side streets where you can park freely, often for unlimited periods of time (excluding street cleaning days). Additionally, at the majority of metered spots you can park freely from 8PM-8AM. In theory, you could wake up every morning at 7:30 AM and move your car to a known unmetered free spot; then repeat every night. Amazingly, a LOT of people do this within various boroughs, so the spots are in demand (I did this for over a year). It seems like too much work, but it's also frustrating to pay $150 a month to rent someone's extra spot, only to find it occupied one night when they're having a large party. Trust me, they'll know you were the one who called the towing company.

What would be helpful is having a mashed up Google maps app which highlights two types of streets: the ones where you can park free indefinitely, and the ones where you can park overnight at meters. A street cleanining day/time note would also be helpful. I think this is feasible if you had a lot of friends to scour the area. Your revenue stream would be ad-based, because a site like this would generate a lot of web-traffic (especially if you hit the majors: LA, NYC, chicago, SF, boston, etc). You could even charge for a subscription mobile app (or just create an iPhone app and pocket a bajillion dollars).