Very interestijg video links!
My conclusion about his shooting style: He has learnt he can get away with the way he does it, and he is being fueled by the recognition he gets. In the end, it's the pictures he takes that provide justification for his ways. Also, it seems he can connect very well with people, and that also helps in situations that could border to being embarrassing.
I have on several occasion attempted to take on a similar style of photographing. For me, this only works if people are in large crowds, and are distracted by some kind of an event, e.g. on a fair. To experience success in such situations provides enormous reassurance, and helps you do what you do with more confidence. And if you're in that state of mind, you'll be able to better connect with people, because you don't feel defensive.
Try it for yourself - it's an exhilarating experience.