Very interesting
To clear this up, yes the coffee man is the grim reaper. I think that what he's talking about with the self serve thing and not having to wait, and killing the woman without having to wait, is because rather than sit there and wait for her to die he decided to just kill her with the cement block -- take the self serve thing and be done with it.
And the dress at the end is (I think) the "strange man" (or the grim reaper) "changing his ways." (beginning to like wearing dresses?)
I like the dark mood, and it seems to be near the same disturbing quality as David Firth's stuff, except with a different stylistic flair. (with things such as the mouths)
At first I thought the guy had some growth on his face, and I was caught by surprise when it ended up being a mouth. great job.