The Daley machine has been very effective at building infrastructure, adding housing stock, and attracting investment to the city. It turns out that a lot of people are willing to overlook some corruption in exchange for results.
(It helped that the Daley family always kept things relatively clean when it came to their own affairs. Most of the serious corruption happened one or two levels below them.)
As someone who purchased every edition of Microsoft Flight Simulator from the beginning, I am still salty about Daley bulldozing Meigs field in the middle of the night.
From what I can tell, a 10x return over 75 years is about a 3% annualized return. That's not a tremendous return during the Zero interest rate phenomena. It's almost a money loser in today's environment.
I do understand the concern about not being able to repurpose the parking spaces, etc. but somehow having been involved in repurposing discussions, I seriously doubt Chicago "Motorists" will ever let a parking space be repurposed into anything else.
Is there another kind?