Here is why I think that Tobi is doomed and will not win in the fight against Naruto 
If you look at the whole manga, you will notice that two main antagonists cannot coexist for an extended period.
When Pain appeared, Orochimaru was doomed.
When Tobi appeared, Pain was doomed.
When Madara appeared, Tobi was doomed. I think it's about time for him to go!
Now, if you agree, then an interesting question appears: who will replace Madara?
And here's my theory, but if you want to guess, then respond first
If you look at the whole manga, you will notice that two main antagonists cannot coexist for an extended period.
When Pain appeared, Orochimaru was doomed.
When Tobi appeared, Pain was doomed.
When Madara appeared, Tobi was doomed. I think it's about time for him to go!
Now, if you agree, then an interesting question appears: who will replace Madara?
And here's my theory, but if you want to guess, then respond first
Madara will be replaced by Orochimaru. It has already been hinted many times in the manga that Orochimaru has been studying Akatsuki, Tobi, and Madara's power. The secret scroll that Sasuke has obtained suggests the same. So, I think that the manga angagonists will run a cycle: Orochimaru, Pain, Tobi, Madara, and Orochimaru again.