There is no reason to believe the OP would have the distance some ridiculously large amount. Sasuke's range limit is around 100m I believe. Obito gets blitzed. You believing the distance would be long when OP didn't specify is nothing but a biased assumption, biased because you don't want Obito to start in range.
Not even talking about Shunshin.
-Never said he'd cut down the tree.
-Obito isn't immortal. The Juubi being inside you doesn't grant immortality, hence Madara saying that he almost got killed by Gai even while the former had the Juubi, and Obito never had the Shinju. It matured into the Shinju when he released it from his body, which Madara later absorbed.
-Based on what? The Juubi evolves by itself. No reason to believe Obito can use the previous forms of Juubi to fight when he's already obtained his own way of using its abilities without being the actual Juubi.
-Lol, the Shinju was evaded by Madara and Hashirama. Sasuke effortlessly evades every single branch and blitz chops Obito in half.
OT: Sasuke wins this one. Gai couldn't outright blitz Pre Shinju Madara, seen when Madara blocked Gai's first attack with his Gudo Dama. Evening Elephant's striking speed, that increases, is what caused Madara to lose the upper hand here. That is the same Madara that Naruto was speed pressuring in Base after his Rikudo Power Up. Sasuke is faster than Base Rikudo Naruto due to his teleportation, so the first moment he uses his S/T, Gai gets blitzed and he dies. Even Post Shinju Madara got hit by Sasuke using his teleportation in two instances where he failed to react.
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Either one means death for Gai. He isn't reacting. People say that Night Guy one shots, but Sasuke simply teleports behind Gai and stabs him in the back.
Juubito is even slower than Gai, so a few seconds after Gai dies, Juubito follows.
