For cities that haven't switched to shared muni-meters, the existing parking meters seem like the natural place to add hardware that checks for availability. If the meters are network connected then at the very least they could report back whether or not they are in use or "expired". A lot of the newer meters allow for credit card payments so I'm assuming they have some kind of network connectivity.
It'd be awesome if a city provided this data to the public. Then anybody could just make an app/website[3] that shows the closest place you can park. Forget trying to make a buck off of reselling your existing spot, the savings on traffic, pollution, and frustration would justify it (less needless circling).
[1]: All spots would be even better but I'm assuming a spot that doesn't have a meter isn't going to have any hardware there that could tell whether a car is present.
[2]: http://en.wikipedia.org/wiki/Muni_Meter
[3]: Or even better integration with your smart phone's existing maps/nav app.