I actually saw "Annotations" as the heavyweight in this trio. "Dog" was fun, "Drowner" was interesting, but "Annotations"—despite its comic format—had some real emotional depth. The hints about what had happened to the man's family struck me as really gut-wrenching, and all the more so because they were never fully explained. The flippant tone seemed to be hiding a loss so devastating that it has caused the man to give up on everything. Sometimes, things are so awful that comedy is the only option; however, it's not the kind of comedy that makes you laugh genuinely, more the kind that makes you laugh with wild desperation.
It reminded me of that classic Pseudopod story—one of my favorites of all time—whose title I can only remember now as "Werewolf Questionnaire" (not the real title). Seriously disturbed emotions masked by sarcastic flair.
Also, I thought the second-person was appropriate in this one, because the narrator was basically taunting the protagonist/victim and saying, "You, yes you, have more darkness and despair in you than anyone could imagine, and you are going to do this terrible thing because you're too weak to stop yourself."