Ideally, any privatized resource would be something where you would bring in competing companies that would pay a fair price incorporating capital and other costs.

In practice, it gets very sticky, and the process is ripe for corruption. Also, there are many things where it's not easy to see how competition (essential) can occur. When I was arguing for private solutions back in college, the case used to show me it couldn't be done was the phone system. What competitor would run duplicate phone lines around the country? While the phone company "breakup" was a half-assed solution, eventually the real answer came when cell phones came around. Cable companies were the same until satellite showed up. Solar power may one day loosen up power utilities. It's amazing how people can find a way around these things. Still, it's not simple. Market economics never is.

Market forces are necessary to keep prices and services in line unless a service is so heavily regulated that is might as well be a government service anyway. When you don't have them--either with a government monopoly, or a government-generated private monopoly, things don't work very well. It really doesn't matter if the service provider is the government or some theoretically private entity.

Another other major problem in privatizing government resources is that the price paid to the government for the resource is often unrealistic. The government has been famous for many years for giving away forests for lumber, mining rights, and other rights to exploit public lands at prices that are sometimes a century old, and are often grossly lower than what any sane private owner would have asked. The resulting waste and overconsumption is inevitable.

Key to any privatization should be a fair price, incorporating true costs. Also, if the resource is not one that lends itself to competition (selling to several different companies) there should be limits on the contract length. 75 years was an insane length of contract for that parking meter deal, particularly for something requiring minimal investment from the company involved. I would have set it for a trial period of a few years, with the option to rebid if the company screwed up. Lease, not own.

Parking meters are a crappy target for privatization in the first place. The supposed purpose of parking meters is to support building and maintenance of the streets and control access, a public function. Unless the streets are private in the first place, it doesn't even make sense. This was a payoff of some kind, not a real deal. But then, it is Chicago.

The Alligator Alley thing was also ill-advised. You're seeing this kind of thing from desperate governments who want cash NOW NOW NOW to salvage their stupid fiscal policies, and don't really care what happens five years down the road.