I think that had Itachi never broke out of Kabuto's control the war would have been won by now by the villains. If Itachi and pein would have been attacking they would a been the hardest to seal. Add Madara and Kabuto freely doing what he wants without worrying without worrying about the Uchiha brothers. Had they still been under Kabuto's control Kakashi would a never been able to save Naruto from Tobi. Kakashi would a been too busy fighting Itachi (being that him and Gai have the most experience fighting Itachi). IMO the villains are winning high diff. It would a been low diff with them on the battlefield
your whole argument is unnecessary though. If itachi had'nt been broken free of ET, then bee and naruto wouldnt have had the needed power to overpower nagatos attack (was it almighty push or his absorption tech? i'll have to look it back up.) meaning they die. At that time i believe their were still clones out and about helping the shinobi, so they are gone most likely leading to aforementioned shinobi being slaughtered by the enemy. However, in that scenario, i see kabuto still dying probably because upon narutos death, the 9tails is released somewhere into the world, and tobi then goes ape s**t on kabuto for allowing it to happen, and given tobis OPness, its very likely he would be able to seal all of the ET after kabutos death, including itachi and nagato.