I wouldn't say is set in Chicago. It's more "Chicagoesque". Yeah some of the buildings are represented, and certain Chicago landmarks are thrown in, but like OP says, the layout is all wrong, and many major landmarks are completely missing. Like the Field Museum, Soldier Field, etc. Now they probably ran into licensing issues with a lot of this stuff, but as someone who's more or less familiar with Chicago (grew up in the suburbs), the game doesn't feel like Chicago.
It's like they bought the rights to use the name "Chicago" and rights to certain other landmarks and buildings, but just made up all the rest. Sort of a fun game, but when a game claims to be set in the city of Chicago, it should fucking look like it.
I wouldn't say he "joined the fight" against patent trolls. He was sued by one and decided to very loudly and publicly fight it - in part so other podcasts aren't put out of buisness. Hence the Fund Anything campaign etc. I listen to his show often, and it's a constant topic.
More power to him!
I think the GP's point was that if it's taking him twice as long to take tests, when he has to apply the information in a real-world setting (i.e. a job) he's probably also going to be slow. Perhaps unacceptably, depending on the job and the employer.
But that doesn't mean he shouldn't be able to get a degree and still apply it with the right job and employer. Good that he's trying to better himself at any rate.
It's later than you think, the joint Russian-American space mission has already begun.