Summer 2017 I finally got to skate NYC (had been to LA countless times, SF, Barcelona,and more). I left my friend's house in Brooklyn to explore. I was surprised at the changes in elevation, and before I knew it was "bombing" a hill. Saw a super hot chick on the sidewalk, then hit a pothole and flew off the board- ripping my pants literally within 5 minutes. It was pretty embarrassing but hilarious.
Anyway I think the most underrated part of why NYC is hard to skate is the sheer amount of people walking around. That said I only stayed in Brooklyn and then Manhattan just blocks from Columbus Park.