1) I was part of the Chicago 2016 team as my club was going to host the shooting sports events (we were looking at getting about $20 million in facilities and the USOC had put it out that if they were going to spend giant piles of money on facilities, they wanted to make sure that there would be follow-on usage. Not just one and done. My club was all on board with the "We'll use the the hell out of everything and anything you build for us" plan. Chicago got bounced in the first round of voting. It was somewhat bitter-sweet.
2) Our Liaison to the USOC knew many, many months in advance that Chicago would probably lose to Rio. As she clearly stated "Rio has better hookers."
3) There is an entire cottage industry of folks that go from city to city to work on the Olympic bids, and then once a city is announced, flock to that city to "organize", build, and run the various venues. Our liaison (shooting sports) was from CA, and she had never been shooting before in her life, until she came out and shot with us (after some training). She had been "organizing" the shooting sports venue since Atlanta, but had never pulled a trigger until ~2012.
4) Best suggestion I heard was to have it (them) in the same place every time. Isn't that how the ancient Greeks did it? Isn't that why it is called "The Olympics" after Olympia, were it was held?
5) I have a bit a schadenfreude for these games. I really would like to see it as one continuous F-up after another, after another, culminating in an utter collapse. Simply because, while there would have been some (okay, a lot) of waste and fraud had Chicago won, you can bet your ass TPTB, would have made sure that everything worked and would have gone-off with a hitch. Capache'?