I've lived in Chicago, so to some degree at least I am used to dealing with big cities. I am used to crowds, and fighting your way through downtown streets, and paying way too much for everything.
But to me, New York was the worst of Chicago multiplied by 100, maybe 1,000. I felt suffocated there. I only spent a grand total of 1 day there and was happy to put it behind me.
I don't understand how anyone can vacation there and find it relaxing. And I certainly don't understand how anyone can put up with living there. I think I would have to end up on a ton of anti-depressants and anti-anxiety pills to be able to live there, even for a short amount of time.
So, for me New York didn't live up to the hype, and I have no desire to go back. But maybe if I was really rich I would see it differently. I think New York is definitely a playground for the rich, and when it comes to vacations they tend to enjoy it immensely.