Itachi mid diff, kabuto was able to beat her with taijutsu and hers fear of blood stuff, itachi definetly can do this too and with much less diff
Itachi loses.
You're comparing a part 1 Tsunade to a War Arc Tsunade. Which are very different in terms of power level. Kishi more than demonstrated this in the War. In part 1 Tsunade uses Creation Rebirth 1 times, used CES, and used Ranshinsho and summoning jutsu and was out of chakra.
In part 2, Tsunade has used Creation Rebirth 1 time, Refilled Gaara's chakra + healed Gaara 1 time, Refilled Oonoki Chakra and healed Oonoki's chakra 1 time, refilled Mei's chakra and healed Mei one time. Used Byakugou no jutsu to regenerate from 3 susanoo sword stabs, 3 yasaka magatamas, and 5 fire dragon heads. She also managed to make an Oonoki with low chakra use the biggest jinton we've ever seen from him 1 time.
So you can't begin to tell be that Part 1 Tsunade and Part 2 Tsunade are comparable in terms of power. There's very obvious jump in what she's capable of doing.
Furthermore, Tsunade is one of the best persons throughout the entire manga with her chakra control. Her medical ninjutsu, her byakugou seal, and her byakugou no jutsu, and her CES, all speak toward the precision of her chakra control. A simple genjutsu is unlikely to hold her.
Itachi's Katon pales in comparison to the one that Tsunade already tanked. He doesn't have anything in his arsenal to actually put Tsunade down. Nor does Tsunade have Hemophobia any longer.
Part 1 Kabuto would be curb stomped by War Arc Tsunade. That's not withstanding that Tsunade was still holding back in order to fight Orochimaru after Kabuto. He didn't really have a way to take Tsunade out of commission. She could have just use Creation Rebirth and been ready to go once more. Kabuto not only fought a Tsunade who didn't use her entire arsenal, and not just a Tsunade that was holding back, and not just a Tsunade with Hemophobia, but a "rusty" Tsunade at that and even then had she gone used all of her prowess against the soldier pill enhanced Kabuto she would have killed him. So I find your use of A>B>C logic particularly problematic.
3 tomoe Itachi really isn't putting Tsunade down. She outlasts him and her arsenal without his MS is more dangerous than his.