Do you think Obito tried to keep his identity a secret from Kakashi, specifically? Like Kakashi is really his only counter with Kamui, otherwise he’s pretty much invincible. His whole plan kind of falls apart at that point. I like to imagine he tried to avoid him at all costs.
Very interesting question!
I think there were many reasons for Obito to disguise himself and that he would have kept his identity hidden regardless. Like, he was a little teen when he first started impersonating Madara. He was smart by influencing people from the shadows, not revealing all of his powers and by letting everyone underestimate him almost all the way up until his plan was complete. I think you're right though, about him being extra cautious about hiding from Kakashi.
Obito had both personal and tactical reasons for avoiding Kakashi. He clearly gets more and more daring though, the closer he gets to his end goal. It's almost like he can't help himself sometimes. Like he's daring Kakashi to figure it all out.
I think Obito has a respect for Kakashi's abilities, being well aware of his perception and analytical skills on top being the one living human who knows him the best, which is sad since Kakashi barely knows him at all. Obito knows that Kakashi could put the pieces together, given enough of a chance, and if that happened too early it could definitely have messed up Obito's carefully laid, overly complicated plans.
Then on top of that there's Kamui. I love speculating about Kamui <3
There's this thing Obito says to Kakashi that I've been thinking about a lot:
Like, Sir... Obito. Mr. Genius Supervillain, please, who do you think awakened YOUR Mangekyo Sharingan? Who did the heavy lifting in that friend-killing moment that gave you your superpowers? Does Obito not realize that their eyes awakened at the same time? He talks in this condescending tone as if it's impressive and maybe even surprising that Kakashi somehow managed to awaken his mangekyo, when Obito witnessed the event. If he truly didn't realize, when did he find out? Was it Deidara's arm?
My point is that I think Obito had enough respect for Kakashi's abilities to be cautious around him but that he also severely underestimated him.
Kakashi could have destroyed the statue and perhaps stopped juubi from ever spawning again, using Obito's own eye, putting an end to all of Obito's plans if he hadn't reacted in time to stop it. Exactly how Obito is able to stop Kakashi's use of Kamui is never explained but I love to think that this could go both ways if Kakashi had the time to figure out how.
The thing is that Obito may act all superior but he actually doesn't seem to know what Kakashi is capable of.
When Kakashi manages to make a cut in Obito's mask I don't think Obito is standing there all confident like he knew that could happen. He's able to hear Kakashi explain his theories to Gai and Naruto and he just stands there, listening. There's so much tension in the way he waits and I think there's lots of things you could read into that. I like to think that Obito listens because he wants to know what his enemies know but also because he hasn't fully figured these things out himself yet. He's way smarter than he was as a kid but the weaknesses that Kakashi are finding in his powers are as new to him as they are to Kakashi. Nobody has been able to attack him from within the void of his own eye-of-the-soul-space before.
Obito was literally untouchable for so long and I think his arrogance made him think that the reduced power of Kakashi's non-Uchiha Mangekyo wouldn't pose a real problem for him. Kakashi could have killed him then and there from within Kamui, Obito says so himself. He calls Kakashi pathetic for having compassion for an enemy. If Obito had known that Kakashi would be able to use his powers against him, threatening his plans and his life, would Obito have killed him? Before the final battle I mean. Like he probably should have? And probably would have? If he truly didn't care whether Kakashi lived or died? If he didn't have any compassion for his enemy.
Anyway I just love how Obito goes on a SHUT UP YOU TALK TO MUCH YOU'RE ALL BLA BLA BLA ALL WORDS SHUT UP AND GET INTO OUR GARBAGE SECRET DIMENSION AND BE QUIET-rant after Kakashi is done explaining it's so in character and he did the same thing as a kid and I mean he's being awful but he's so Obito and it's cute how he consistently gets so annoyed while having to listen to people explain things, it just is <3