I read the first book. The arrogance was a bit much, especially in a book where he's talking about the importance of randomness. But, like you, I did go off an explore about a lot of what he said. So it's a fun exercise.
There are a few great books which are too repetitive. "Black Swan" is one; he could have got all of that into a book a quarter the size and not lost much important. Another one is "Reckoning with Risk" by Gerd Giggerenzer - he takes many chapters to say people don't understand percentages, and you should really use "X people out of 10,000" when explaining risk to people.