Without the interludes, this story would've been funny. It has all the makings of an excellent comedic one-shot. A ray of sunshine in a world where the character of Draco Malfoy is beloved as a bad boy, regardless of his history of cowardice and unrelenting incompetance.
But, you had to go and include the interludes. So I can't classify this as the little snippet of comedy. No, the interludes took this story and made it important. Made it valuable for more than humor.
It showed a very real possibility for a Harry that managed to win before 7th year, a teenaged celebrity without a steady girlfriend, who happens to have the entire poplution of his school (barring a few Death Nibblers) feeling that they're deeply in his debt.
I've seen a few "Harry the Man-Slag" stories, and they just don't seem right. If Harry did decide to date every available girl in Hogwarts, I have to imagine it'd go something like this. And the way you interweaved with Draco's more limited (and deluded) perspective, almost has to be fully appreciated with a second read-through.
I think you disappointed a lot of people with this one, people hoping for something simple or smutty.
Screw them, I say.
Blessed be,
-Brother Bludgeon