From my standpoint, I can see obito breaking very soon. We know that he is the strongest but we know he is vulnerable now thanks to kakashi. This is why I can actually imagine him breaking or giving naruto a window to answer to obito's doubts. However, madara will then use that as his window and opportunity to get that genjutsu world that he wants. Kakashi could very well be there to see obito's breakdown to tnj so I'm not worried about that. I definitely think the attack will hit, that's just my take on it, but I don't think the effects will be very physical from now on. This attack will not stop obito, but it will make it into more of a mental game than a physical one. It's not the final attack for sure.
Yeah, well I did address more in the above post. The above post could happen, but we'll see. In a way, I still see Madara going down Star Wars episode 6 style.