Chicagoan here. The amount of fraud in welfare here is astounding. I regularly go to the grocery store and see people with nicer cars than me using their link card to pay for "groceries." By groceries I mean high-end items like lobster and steak, which they are clearly cashing out the card on and not shopping for food like everyone else. I don't know how they qualify for this, but imagine via some creative accounting that mRelief, I'm sure, is also willing to share.
I don't think people outside of the city realize how bad things are here. The corruption, handout mentality, patronage, politics, public sector unions, etc are probably the worst in the nation and it only seems to be getting worse. The various attempts to build a SV-like environment in Chicago will continue to fail until this corruption is cleaned up. I don't see a lot of incentive to invest in startups here, especially if we factor in our very high tax load and the little public value we get from it.