This is my favorite one of the peephole, he just looks like "Yeah, I'm doing all this crap to you, what are you gonna do about it? I'm out here, and YOU'RE in there"
It's not random. After Eileen Galvin is attacked you have to then go check the Henry's apartment when it's Henry's turn for being attacked. The thing about this game is that you have to check-out Henry's place extremely plenty of times.
I got this on my first playthrough. I wasn't doing particularly well, I remember that Eileen was badly injured and the apartment was in an evil state. I wonder if you this scene is triggered if things are going particularly badly?