Obito is gonna help naruto in the end. Madara's sneaky self is gonna overpower obito because he probably didn't tell obito all his techniques before he died. I mean come on....no one is gonna tell someone their weakness right. Has anyone noticed that naruto's enemies are somehow connected to him they entrust their wills to him. EX: Nagato>jaraiya>naruto.......Obito>minato>naruto
He most likely will get smacked by madara reason being that he's hard to deal with and give naruto his will by protecting the world from becoming trash as soon as he dies.