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Hmm. The Andre win for Big Show seemed to be half "have your moment, Giant" and half "after fucking up with Cesaro we need a guy to win this that has already had a career so we can tout him as a winner with some accomplishments next year." The whole booking of the thing felt weird. When I saw Cesaro out there, I immediately wanted him to repeat. The ending with Miz and Sandow felt weird. I guess the match really doesn't matter in the end, which is a shame, because it could.
John Cena beating Rusev was the right call. Cena as the US Champion is actually interesting, and Rusev can now come back badder than ever before. If he's going to move up the card, he needs to lose that US Title at some point too. People were saying "Rusev should beat Cena and then get a main event heel push." Well, he's actually got a mid-card title. See the problem there?
The more I think about it, the more I think that Bray Wyatt should have beaten Cena last year. It wasn't a death knell for him, but in retrospect, the win didn't really help Cena too much. This year, Wyatt probably could have used the win against Taker. With Brock seemingly transitioning into mega-face, having Wyatt as a mega-heel that has also beaten The Undertaker at WrestleMania? That could be money. Taker also could have rebounded off another loss for a "three strikes and I'm out" moment at WrestleMania in Dallas.
Orton beating Rollins makes sense for the parity reasons you mentioned. Orton has got a great claim to the World Title right now, and he's red hot when he's a babyface. Plus he needed a big win so people know they can take him seriously again. Rollins winning wouldn't have been the worst thing in the world, but it would have left the Rollins/Orton story in the dark a bit.
To answer your real question here: I think it's when the young guy winning makes money for the company. Or sets up money-making opportunities. When the veteran can afford the loss and it tells a better story for them to lose, go for it.
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