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TheMonarch

Naruto's talk no jutsu(plot armor) went off this episode!

Nolli Dee

Obito never got training from madara, his Kamui teleportation/pocket-dimension ability was specific to His Sharingan. So hell yes he 100% would have been stronger than Kakashi. He would have rivaled Itachi and Shisui as strongest among the uchiha at the time. Also Obito spent the entirety of YEARS underground (2-4 minimum) trying to get back to Kakashi and Rin and the Leaf Village. It wasn’t until Madara set up the whole “manipulate hidden mist to seal 3 tails inside Rin then make it rampage when she gets back to her village” senario that made Rin have to decide to kill herself / kakashi not being able to actually save Rin / Obito loosing the one thing he cared about most aside from becoming Hokage. So all in all his intentions have been what Kakashi said, trying to prove himself wrong through showing others pain and suffering.

Anonymous

But didn't Swirly and friend (The two Zetsu Madara had babysitting Obito underground) train/rehabilitate Obito under Madara's orders? Even tho the training wasn't directly from Madara, I'm sure it played a part in making him stronger because he did seem noticeably stronger after the time skip just before he broke out to go save Rin and Kakashi.