Good point - I found this a confusing analysis without digging much into what it was saying - Urbana and Athens were high on the list...why? Do they have public bus systems that students use extensively? If so, that would tend to give a false impression of how much public transit is used there. I liked that he later pulled apart the small and large cities, but it would have been nice to understand what the data was saying in the context of the cities it examined.
Your point on Chicago is well taken - I was surprised to see SF/Oak ahead of it, as they "feel" harder to navigate with transit only, but I was forgetting that the suburbs are included in Chicago, which is basically impossible once you leave the city limits.
#2 is called this: http://en.wikipedia.org/wiki/Buffon%27s_needle. This is also mentioned in Jordan Ellenberg's book How Not to Be Wrong, and has a similar passage with your explanation above. I mention the book as much because it's a great read.
Yeah - It seems strange that the early parts of the article try to paint him as one who has failed but still overcome adversity. It is challenging to argue that at any point he wasn't very, very successful.
It would seem more appropriate to point out that despite his tremendous capabilities, he still has faults and has experienced awful tragedy. The article veers that way towards the end.
Sounds like good people; glad to read about someone with substantial means helping drive education and science.