Raocow/WMG

All of Raocow's videos are thickly veiled propaganda against the Milkman Conspiracy
All of those non sequiturs you have been hearing actually possesses all the secrets and dangers of the Milkman. The most overt message that you will hear about this is in Raocow's first episode of An Untitled Story.

Raocow is not the same person from his Google Video days, but in fact the host body of a malevolent entity that forever changed him
Once upon a time there was a man from French Canada known as Rao. Far off on the other side of reality was an anthropomorphic fire flower, the true villain of Mario, that was so powerful it escaped its reality and entered ours, rewriting the Mario story to obscure itself as a minor element of gameplay. It then infested Rao, mutating him into Raocow, and began a single-minded vendetta against every Mario game ever, playing as Mario in an effort to destroy him from the outside. The gradual evolution of his talkative non-sequitur speech is a major characteristic of how the fire flower continuously erodes his mentality. In addition, every time Raocow plays a game that isn't Mario, it is the true Rao fighting back against his mental enslavement. And that, my friends, is how the chipmunk saved Christmas.

Raocow isn't crazy.
We're the crazy ones.

Raocow isn't finished with Karoshi.
He's parodying the fake endings found in the games.