Kakashi is chump change. Obito is the only tricky one here.
Itachi can one-shot either with Genjutsu or kill Kakashi with Amaterasu since Kakashi lacks the speed to dodge it and cant use his Kamui to phase like Obito can. Then there's Yata mirror and Totsuka blade which Kakashi still doesn't have an answer to.
Sasuke on the other hand has incredible talent utilizing Inferno style. Much like Itachi, Sasuke kills Kakashi Amaterasu GG.
So this is basically the Uchiha bros vs Obito. With both the brothers being on gaurd, it will be hard for Obito to blitz either one. Obito would be on the defensive most of this fight. If he decides to get close he will certainly phase through whatever attack is used on him. Obito will then try to counter attack which he needs to materialize to do. And once he does he would get blindsided by Amaterasu by either brother.
That's assuming Itachi doesn't even use Genjutsu on Obito. And since the OP doesn't state any restrictions, Itachi would still have Shisui's eye to use Koto on Obito.
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