I think what annoys me with Obito is that he is constantly dreaming for something he doesn't have. He's like a selfish kid with huge power.
First he is dreaming for a world where there is Rin, because that world is the only 'beautiful' and 'right' world for him. Not once does he realize that if he creates a world where Rin is smiling, it's a contradiction to what Rin really is. Because, there is no way the 'real' Rin, who sacrificed her life in the village, will be smiling in a Tsukuyomi World created on the sacrifice of the people she swore to protect. He's selfish and he forces his own ideal Rin into his own ideal world. But that's not really caring about Rin. That's only Obito trying to satisfy his hunger for what he doesn't have.
Now, that the idea of Tsukuyomi is getting less and less likely, he is starting to dream of the 'what if' scenario. He's starting to think that maybe he could be happy in the 'what if' scenario. But the 'what if' scenario only looks bright because he never had it, and he's the guy who keeps chasing for something he doesn't have. If he actually was in that situation, he would never feel content, and he wouldn't appreciate his friends like in his imagination.
His childish fantasies are downright disastrous.
Obito and Naruto is so similar, yet so much different in a way that Naruto actually appreciates what is given to him, and doesn't force his ideals (for example: Sakura).
Same problem that Sasuke has, also Nagato had(My pain is greater than yours, famous line), Madara also has this too, Orochimaru another one.
In fact all the villains are selfish.
Sasuke is like this because he thinks he's special and a victim and that no one even Naruto knows what he went though and he uses the excuse "his clan disaster" to justify what he's doing so far, much like Obito using "rin" as an excuse, and Madara ("his brother death"), and pain ("Yahiko"), Orochimaru ("Wasnt chosen as a hokage").
Excluding Orochimaru, the rest wants to bring peace obviously on the wrong manner but uses their own disasters to justify their evil actions.
Edited by Dαrkrєrsŧ, 24 October 2013 - 06:01 PM.