Here's the pilot's YT channel¹, and one of the videos that triggered the fines: https://www.youtube.com/watch?v=MQx6xhSSKco
In my eyes, DJI application’s UI is as much (if not more) to blame here. It puts way, way too little emphasis on FAA regulation violations; a small corner alert when entering a controlled airspace is IMO inexcusable (“Fly with caution” and then it disappears). Generally speaking, the app knows everything necessary—location, country, time of day, lighting conditions—to show a big “Only proceed if you are indoors, outdoor flight is subject to $xxxxx fine” warning before flight takes place.
All models in the past five years come with a 120m max altitude set, and an absolute 500m limit.
There is a huge buffer area around airports [1]. If you’re seeing the “fly with caution” warning, you are not in a controlled zone. This is purely a matter of regulations.
I still think DJI UI is designed to enable fineable violations. The app at least knows it’s night and middle of a city; perhaps it can’t infer missing line of sight (questionable), but nighttime flight alone outdoors in a city is already illegal without a permit.
A company like DJI could easily afford to scrape and aggregate UAV regulations from different regions (there are numerous websites doing just that already) and integrate relevant checks in the app.