My ex wife and I did Times Square New Years for our first anniversary. That was in 2005. We stayed at the Marriot Times Square(and could only afford it because her mother was a Marriot employee with a significant discount).
We tried to go out around 9 to find a place in the crowd. It was awful. Absolutely nuts-to-butts and not with the finest of humanity. We went back inside after a half hour tops. Turns out there’s a revolving restaurant at the top of that hotel called the View that was having a party. We had a lovely time up there. New York City possesses some real gems in the museums and arts but the rest is a was a crap hole 20 years ago and it hasn’t improved. I don’t ever want to go back.