It's really hard to come up with a deal that does a better job at effectively preventing any changes to road and street infrastructure.
However, municipalities with a good credit rating can usually issue bonds that pay out about a third less yield than treasuries, thanks to favorable treatment of municipal bonds in the US tax code. I don't know how healthy Chicago's rating was in 2008 but even if somewhat mediocre, it's likely they could've gotten 3% or less on the bond market.
So at a minimum there was no advantage for the city in signing up for a sweetheart deal with strings attached, instead of covering the shortfall by issuing a bond.
In any case, if it was 3% it's economically very comparable to issuing a regular bond and not the "fleecing" that's talked about. If the city regrets the deal, it should be able to issue a regular bond and use it to buy out the investors, or issue regular bonds annually and use them to pay the penalties, all at roughly a wash economically.
I'm not sure 3% is correct, though. I'd like to see another source on that. It reads like it has some protection against inflation. If it's 3% + inflation, that's a really enormous return.
As for “normal returns”, it was sold well below value, and the whole enterprise is literally just rent seeking.
Typically I'd think of a city having a contract with a service company for them to manage and service a city's parking meters for a cut of the revenue, "the city in control of its subcontractors".
This reads very much as the City of Chicago tightly subcontracted to maintain the 72 year revenue stream of Chicago Parking Meters LLC, "the tail wagging the dog".
There's much to be said for tying some form of liability to office holders who make a deal.
The book "Paved Paradise" by Henry Gubar that was the source of the podcast, looks an interesting read:
https://www.amazon.com/Paved-Paradise-Parking-Explains-World...