Somehow I feel that there is a possibility for Obito to lose patience and just cast the infinite tsukiomi, but when it activates only a few people resist it in some way like obviously Naruto due to kurama and Sasuke having his own powerful eyes, others could resist it as well, but I would suspect a situation like this to arise if Obito gets over whatever it is Madara is planning and after the other kages come back.
This would be an interesting part if the eye of the moon plan goes full steam ahead and brings another arc upon us like the dream world arc or infinite tsyukimoi, whatever you feel, but I would suspect Naruto, Sasuke, Minato, and a handful of others to intially resist it but it would be a test of their ultimate desires vs they know whats real and not real,
Naruto it would be much like road to ninja with all his problems solved and being hokage
Sasuke it would be having his clan back
Sakura it would be team 7 being back together
the list goes on, but ultimately Naruto and friends would need to break out of this and basically resisting Obito's world and giving him a speech about how none of this is even right, all it proves is how weak willed obito is, how especially the one person he loved, it would basically be Kakashi's speech to Obito from 631 about those who ignore what their friends say or feel are even worse then those who abandon their friends. Basically the nail to hit the hammer in Obito would be, Rin would ultimately never love or approve of what he did, making a mockery of her with an illusion world. Something like that would hit obito harder than any rasengan so far.