I keep getting the vibe that people think Obito is a pedo or weirdo in his original resolve to reunite with Rin.
He's not. In Infinite Tsukuyomi we saw people can dream in alternative timelines so it would make sense that Obito's dream was to see a world where he wins the love of a future Rin, not exactly young Rin. He was merely chasing the idea of Rin, not child Rin.
Also, when Naruto calls him the "coolest guy" I think that meant Naruto wanted to say he understood Obito. That means that he knows what it's like to keep emotions to yourself and feel loneliness so in that way, he'd would've wanted to be his friend. It's not literally that he's better than anyone Naruto has met but that he was the one of the few people Naruto could exactly connect with.
He's not. In Infinite Tsukuyomi we saw people can dream in alternative timelines so it would make sense that Obito's dream was to see a world where he wins the love of a future Rin, not exactly young Rin. He was merely chasing the idea of Rin, not child Rin.
Also, when Naruto calls him the "coolest guy" I think that meant Naruto wanted to say he understood Obito. That means that he knows what it's like to keep emotions to yourself and feel loneliness so in that way, he'd would've wanted to be his friend. It's not literally that he's better than anyone Naruto has met but that he was the one of the few people Naruto could exactly connect with.