Was he really competing against the Third? DB's subs say that he lead a party that was against the Third's policies, making him something like our opposition leader, but it doesn't say he was in anyway strong enough to compete for the title Hokage. Shikamaru shows his wit again, he didn't waste any time. While it looked like they were observing Naruto's fight, he sent out his shadow to assist.

I didn't notice Sai's clothing much at all really. It's mostly in the ED that I tend to, and even then it's not making an impact anymore. This pissing Naruto off part, it's just as when Team Kakashi first started out, only difference being Sakura was drooling over Sasuke.