Intel is manga. I'm a pretty new member, so I didn't cover all my bases in the first post and didn't restrict some of the stuff that should have been. Sorry about that.
Anyway, my personal opinion is that Orochimaru and Kabuto win. People seem to forget that Orochimaru nearly did escape Tsukuyomi, Itachi just cut off his hand before he could. That's actually an incredible anti-genjutsu feat, being capable of movement during Tsukuyomi and nearly escaping it. If Itachi tried to put him in Tsukuyomi at such a long range, he wouldn't have the change to cut off his hand, and even if he did at close range, his hand getting cut off doesn't matter anymore. Oro can regenerate his limbs, like how he regenerated from being literally bisected by Four Tailed Naruto. Once he gets out of Tsukuyomi, or when it ends if he's kept from doing so, he's back in the fight and Itachi can't just spam Tsukuyomi without depleting his chakra fully.