Of course Tobi knows what he'd doing. He and Madara had been planning this out for decades. He has had such an array of backups that Naruto is going to have to work his ass off even more to win for sure. And then there's always the possibility that Tobi will do what Kabuto and Shika suspect he'll do if he has to: create an inferior Jubi with Kinkaku and Ginkaku's complete (Yin/Yang wise) chakra and the one tail worth of Hachibi he has. When his plan inevitably fails, it's not going to be because of a stupid oversight or something.
/first Naruto Base post
/first Naruto Base post