This is not one of those flight simulator joy rides: it’s the real thing.
There is a corridor of completely uncontrolled airspace that runs right through New York City—the Hudson River Special Flight Rules Area (SFRA). As long as aircraft stay strictly within the corridor and altitude between 1000 and 1300 feet, they operate under no air traffic control in “see and avoid” mode, obligated only to report their position with respect to certain landmarks. This allows spectacular views of adjacent Manhattan Island.
Living and flying out of northern NJ in the early 1970’s, I made this flight many times, mostly at night. At night, it is like looking down into a lighted jewel box. I often took first dates on this jaunt. Commenting on the effectiveness of this approach would be unseemly.
On demand side there is big money (many foreigners looking to invest/stash or indulge). It favors great views (high perimeter to floor area ratio and height) and bragging rights (tallest thinnest…).
On the supply side there is regulation (limited land available due to rent control, etc.; setback requirements; air rights requirements…).