"Tier whoring," I think, is actually pretty interesting. By picking the best character in every game, I think you're removing the wall that might hold you back by picking a shitty character. It's like N-O. What if he picked up Eddie (of course this might not be a good example because N-O might only be as good as he is because of venom)? What if Daigo picked up someone like chun li (not bad, but certainly not the best)? He would probably lose a lot more.
By playing top tier, you really start playing the game with no excuses. If you lose you got outplayed.