He was right, y'know. "I photograph to see what a thing looks like when it's been photographed."

He was described as "an almost obsessive picture-taking machine."

I don’t think there was any “almost” about it. I’ve always felt that towards the end of his life he became mentally unwell, hence the hundreds of unprocessed cassettes of film thrown into drawers and the almost gabbling nature of some of his interviews - nothing “measured”. At that stage there was no seeing “what a thing looks like when it's been photographed” as he never looked any more. Very sad; think what he might have done in this digital age.

I still think his attitude to photography is worth emulating, though.

Thanks. That is a valuable addition. Many artists have great productive periods when their output is wonderful, and other less distinguished periods. But what you tell us about Winogrand is tragic. I must examine his street photography of the 1960s in New York City. That is held to be his pinnacle and so expressive that it defines ‘street’ to this day. He did get right in people’s faces though. Perhaps not the most sensitive of men.

Photographers like Diane Arbust,David Hamilton,Francesca Woodman,Kevin Carter,Garry Winogrand etc..they did amazing work but payed with their sanity..in a way its a history of art,the history of anxiety.
Without angst art wood be like a soup without spice.