[gandreani]

The only complex part should be gathering the data (how many spots are open in this street at these times).

I bet in most places these things are measured, and if they aren't it could be simple to measure. LA has parking meters that take credit card payments. You can extrapolate parking spot availability from that. Obviously I'm ignoring the cost of adding credit card parking meters where there aren't, but it proves my point that it could be simple

Choosing a price doesn't have to be complex either. Every quarter raise the price until the desired free space is available

[jandrese]

Does this system retroactively raise the price on cars that are already parked there? Or does it create an incentive to get their early and park as long as possible since you'll never find a spot this cheap again?

[gandreani]

Sorry, wasn't clear in what I imagined.

Every single street parking meter I have ever seen has working hours (including holidays) and constant price to pay. There's no price increase in certain hours of the day or that sort of thing.

The price adjustment would be changing that constant price per quarter of the year.

So you don't get there early in the day or hog a spot. Every one pays the same regardless of what time they want the spot during the working hours