Whenever I walk in Central Park in the evening, I pay attention to how many windows of adjoining buildings have their lights on, as a rough proxy of current occupancy. Billionaire-class buildings like 15CPW, One57, etc. are often 80% dark. On a holiday weekend like today (it’s considered lame to be stuck in the city -- you need to be in the Hamptons or wherever), they can be completely dark. I’ll go check in a while. My building on the other hand will be lit up like a Christmas tree.
I wonder if there's a cool data science project here. On a repeat basis: take a picture at night, do some basic CV on it, and output an occupancy rate. Might be interesting for some of the luxury buildings you've noticed.