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The way I see it;
Itachi genjutsus konan and ends it there with incap or death depending on genjutsu used
Kisame tanks majority of konan's paper jutsus with Samehada blocking and absorbing her charka considering their speed he should be able to get in close enough to do so or can also use massive amounts of water to neg the paper.
Pain really at a disadvantage here, if itachi and kisame push up on him itachi will easily find out that shinra tensei has a cool down and form a plan with kisame to win, probably something having to do with samehada and amaterasu. I think the only thing helping pain is his speed so he could definitely catch them off guard with it and shinra tensei them.
Round 2.
Itachi absolutely spams amaterasu (spreads) and kisame likely gets negged by absorption path and asura path.
Round 3.
I think round 3 Pain can win against them, given kisames best ability in samehada is his bubble shit it'll get absorbed and basically just have a strong kisame .