The nicest way to interpret this comic is that Randall knows that he can be annoying and preachy and this is his way of acknowledging it and thus, in theory, making it more OK. Whether that works is up to you, I suppose. I don't think it does.
Whenever I wonder if I'm really interpreting a comic right or not (in this case, Is Randall being mildly clever and ironic, or is he just oblivious and hypocritical?) I of course head out to the dreaded xkcd forums. Today's comic has had surprisingly little discussion - only 78 comments, putting it third on the list (usually the newest comic is first, occasionally second). There was hardly any discussion of the comic at all, and none about how Randall himself recently skipped comedy for a day to complain about itunes. Instead, they debated whether 0.999.... equals 1 (most of these posts have since been deleted, but evidence remains). Also the merits of Battlestar Galactica. Also whether Let It Snow is a christmas song. Idiots.
Speaking of Let It Snow, why did the first panel use its first line? It doesn't really set up anything about the joke or relate to the rest of the comic. It just makes you think the comic will be a song parody and leaves you (ok, leaves me) confused.
And of course, a relationship that is breaking up over DRM is pretty damn quirky, wouldn't you say? Not to mention just another depressing messed up relationship comic. I'm going to have to make a new category page for that I think.
update: A few commenters point out something I really should have noticed at first: This comic is, in addition to its many other flaws, very very similar to Comic 473. The rhythm of it is the same - four panels, the first three are basically serious and vaguely sad about a failed relationship, and then the 4th shows that the breakup was over a trivial issue (har! that's funny!). Not only that, but they both have basically the same image in all four panels. What the hell randall? It's been less than 3 months!