My $0.02 on psychology:
Given his furtive, rat-in-the-shadows behavior, he is NOT a Dean K-type attention whore. No entourage, no fanfare, not a sign of any friends or even his wife at the end of the race, just slipping in and out as inconspicuously as possible, trying to hit the mats, getting the numbers right thane hightailing it out. If he was planning a future of a book, speaking tour, etc., we would see more evidence of documenting with photographers instead of avoiding them, we would see some film-making, that sort of thing.
I am getting the vibe of a pure compulsive cheater, like the rich guy who compulsively shoplifts for the rush, the guy with the beautiful wife who cheats with much less attractive women, and so forth, all for the challenge and the buzz of being a near-criminal, but in this case not quite doing anything actually criminal (unless fraud comes into this with the charities).
I have no doubt that Kipper himself is getting a good hit off of this thread, even as the noose tightens on his little escapade.