I know that it's mostly in fun, poking fun at him, but I do think that we should feel for Kip.
He's set out his stall as THE most pessimistic fan of Oxford United, more like a glass 90% empty sort of person. So he really doesn't get to experience the depths of despair the rest of us go through when we lose--he knew we'd lose all along.
But, like all of us, he secretly would love to actually support, positively, the team. Because he knows that any fan who actively supports a team and is optimistic about their chances each and every game, each and every season, is doomed to disappointment. So what better than to choose a different team each season to be over optimistic about, just to experience the lows of that optimism being for naught? This year it's Charlton. Good for you, Kip