A sorta prediction: Obito is trying to crush Naruto's will. To ensure to himself that anybody that was like the old Obito inevitably becomes sick with the 'actual' world.
Naruto will- either falter for a bit and get out of it, or will get out of it.
Obito will be dumbfounded and cannot accept this. He will either try to assert his own path by reviving Madara so that the plan can be completed (in other words, he'll snap), or defect like Nagato (but I doubt the latter, Obito is truly warped beyond having 'ideals').
Just a guess. I liked the chapter, coulda done Neji's death a bit better, but looking forward to next week 4/5