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While SasuNaru is fairly popular, I don't think it will happen in the series, just because (as previously pointed out) there are no gay people in the show, as well as they always refer to each other as either best friends or brothers. And while Sakura didn't go look for him, she didn't because, though I love her to pieces, she's weak until two years later when she DOES look for him with Naruto like promised.
*Ahem* Now back to the original topic.... Of course, it will be close, if Sasuke doesn't go with Orochimaru, it will be done right before, so really there is no way to tell. I think that Sasuke will realize what's happening (if he doesn't already) and decide to screw Orochimaru over and look for Itachi himself, but I don't think he'll go back to Konoha easily either. I think he'll still be on his own. Sasuke is too important to loose as a character
*Ahem* Now back to the original topic.... Of course, it will be close, if Sasuke doesn't go with Orochimaru, it will be done right before, so really there is no way to tell. I think that Sasuke will realize what's happening (if he doesn't already) and decide to screw Orochimaru over and look for Itachi himself, but I don't think he'll go back to Konoha easily either. I think he'll still be on his own. Sasuke is too important to loose as a character
I like your idea! I think this is fairly possible, and I agree with Sasuke going alone to look for Itachi, seeing as he would not want to return to Konoha.