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I'm going to break this down.
1] Samehada is a sensor [You must be registered for see links]
2] Sensors are able to distinguish whether they or someone else is under genjutsu or not [You must be registered for see links]-[You must be registered for see links]
3] On it's own, Samehada can sense/distinguish Kisame's sense of urgency without Kisame prompting it to do anything [You must be registered for see links]
4] Samehada transfers some ofYou must be registered for see linksinto Kisame to disturb his chakra flow thus breaking Kisame out of any genjutsu [Not including Tsukiyomi]
Furthermore, Itachi isn't by any means defeating Kisame 'easily' as you say. It will be with nothing short of high-difficulty for Itachi to bring someone as monstrous as Kisame down.
No. It was able to smell out Kisame's Chakra like a dog sniffs out food. That is all, no implication whether Samehada has the intellect to tell the difference between genjutsu and reality when it dosent even have a thought process.
Human sensors with intellect and knowledge on genjutsu can tell reality and genjutsu, not living swords who only act on instinct, not judgement.
Just because Samehada can sense if Kisame is in despair, dosent mean it will know exactly how to fix the problem.
Samehada can give chakra, as in replinish, this dosent auto mean that it disrupting chakra flow.
Itachi wins pretty easily. Sorry..