We don’t know at what altitude the drone was flying, it might have dipped below the rooftops between homes and may have been fifteen feet above the ground, that’s when he got it. Most of these commercial drones feed video back to the controlling source, no?
I only have a little DJI that I use for personal stuff, like taking third person shots of family outings in scenic places. I have used it to aerial survey my roof, my immediate neighborhood, etc, but again, just recreational stuff. As a non-licensed operator (not required for my drone), I am not supposed to ever let the drone get out of my direct sight, though the radio link is capable of controlling it beyond where I can still visually see it and I have transitions to the video link. Most of what I have used it for has been inside of a mile or three.
To answer your question, likely yes, though I dont know how the rules change for commercially licensed operations. As a practical matter, for safety of persons on the ground and the drone itself, I dont think the drone operators would want to be operating close to the ground except to vertically insert the delivery and then vertically exit the area. Is it possible to lose the video link when below the roof lines? I would think its highly possible.