Well, it looks like a typical CFIT......
I don't know how people fly at night but this idea to be in contact with the ground all time is....impossible.
You have to stay around urban area or town to be able to do that.
How would you fly EMS doing that?
The fact is, the FAA and Transport Canada have regulation who make no sense, are not appropriate to any operation, and of course, refuse to change it because they perfectly know the consequences.
In many places, you go for a night flight and a big part of this flight is done in complete darkness. In reality, a night flight is an instrument flight and nothing else.
We go to many places where it does not matter looking outside because you won't see anything. Of course, now we have NVG"s, so we see everything.
But, I flown for a very long time without them and what you do, is an instrument flight.
Looking at one lonely light somewhere won't help you anyway, it is the best way to get disoriented.
The FAA and TC know that perfectly well, they know what everybody is doing, but do they change anything??