Set up inexpensive wireless cameras pointed at all street parking spots in the city. (doesn't have to be wireless cameras - pick any method or device that can reliably detect whether a parking spot is empty, cameras are the most flexible). Feed that data to a server, then dish it out to mobile devices (iPhone, etc.) combined with GPS to find the nearest street parking spot. Bonus points for intelligent behavior like not sending two cars to the same spot, or considering which spots are likely to be filled by the time you get there and what other spots are around. Mad bonus points if you work at a high enough level that this feature gets built directly into new cars.
I guess "outlandish" is a bit strong, it feels like it's only a matter of time.