Obito will end up in his own dimension forever.

[a banned cartoon]

It make sense that Obito has Kumai, it's another dimension, he wants to create his own world, but watch the Genjutsu that he creates end up turning on him. He'll end up in his own eternal Tsukinomi inside of his Kumai, Im actually starting to see where Kishi's going with this.

 

[Darth Vader]

Well, you don't know where Kishi is going. So...

 

[The Necromancer]

He can't travel to the kamui dimension while he's the juubchuriki. So he can't do both.

 

[a banned cartoon]

I believe somehow Madara, and he will be the only ones ending up in the Genjutsu, inside of his Kumai dimension. If you really think about it, it makes sense that he's got his own dimension to escape his shitty reality.

 

[a banned cartoon]

He can't travel to the kamui dimension while he's the juubchuriki. So he can't do both.

Where has this been stated?

 

[The Necromancer]

Where has this been stated?

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[Shinobi2012]

Where has this been stated?

It has been noted that he can't or at least is having trouble using it as a jinchuuriki
I do see what your getting at and i like the idea.
As for how it happens,whether it be him doing it on his own accord or gets trapped in it ?
Both ideas sound interesting,definitely a break form the pack.

 

[a banned cartoon]

Oh well the Juubi's actually no longer in him if you think about it? Still the fact that Obito hates reality, and he has his own dimension. Kishimoto's foreshadowing.

 

[FitzChivalry Farseer]

Its been predicted before

 

[Mr Hiru]

What's Kumai? XD

 

[B00m]

But Naruto needs to conquer/TNJ over his extreme opposite, I guess he could still do that before hand. I find your idea to be very possible though. I can see the Jubi denying him of being in control and trapping him much like Obito did to the Jubi, kind of a switcharoo like Sasuke and Orochimaru.

 

[H a n]

I think he will just be dead..