1timeonly
Let me just say you did brilliantly by highlighting Itachi's abilities, but you needed to elaborate! You did an excellent job of telling us what he could do, but you didn't properly explain why or how he could use this to his advantage!
Your opening argument was more or less strong, but at the same time, it contained many flaws. As the other two have already mentioned, the Databook accurately records Itachi's stats with the MS, thus making your original argument less reliable. Your terrain argument was actually quite clever, although I do not think it would have helped your recurring debate with Draegod in the long run, it was however, a nice addition. Your ninjutsu claims are more or less accurate, as Suiton indeed overpowers Katon, just as water conducts electricity. I did, however disagree with you Tai/Kenjutsu claims. While Itachi has shown to be extremely proficient in wielding Kunai, Sasuke, while facing Yamato, disproved your statement. Draegod never mentioned it however, so it's all good. Sasuke was easily able to channel a lightning current through his sword, rendering his Kunai useless. The same method can be applied against Itachi. I wish you would have elaborated on your clones section, to be honest. You did an excellent job of explaining it, but you lacked in detail as to how Itachi can countermeasure Sasuke's attacks. Just claiming his clones can be used as a distraction while Itachi can counter his Ninjutsu is simply not enough for me.
While indeed Itachi is superior in Genjutsu, Sasuke has really shown the efficiency to counter or break all Genjutsu, should he exhaust his 3T enough. I wouldn't count on Itachi having Sasuke in a Genjutsu, especially since Sasuke has already been shown to break Tsukuyomi. On the positive note however, your counteraction of Sasuke's shuriken jutsu was spot on, I'd say. It's true the MS is what impaired his vision, and with superior reflexes and speed, this won't be a problem this time.
What really caught my eye though, was your lack of elaboration. You would make a decent opening statement, touching on methods which could prove troublesome for Sasuke, but then you just stop. The lacking detail just wasn't enough for me. Your KA claims are futile, as it's triggered to react to Itachi's MS, which is restricted. The rest of your rebuttals was stationed on countering everything Draegod is saying, where I believe one should take the debate further, instead on fixing on a few things. This debate at one point became centered around whether Itachi can counter Manda or not, move on, and carry on with the debate.
Draegod
Your opening lines concerning the location wasn't needed at all, as they supported no further claims in the rest of your argument. As well, you seem to have forgotten Sasuke hadn't aligned himself with Obito at that time. Also, while Sasuke may have all or Orochimaru's snake abilities is questionable, and debatable. Sasuke has been shown to use multiple jutsu created by Orochimaru himself, but since Sasuke hasn't actually shown this jutsu himself, I wouldn't think it's quite fair, adding to Sasuke's arsenal when the manga hadn't displayed the said feats.
While it is infact true Itachi has been shown to display late reactions at times, I am inclined to believe it is because of his impaired vision, as seen with Itachi not being able to properly dodge the shuriken. This, however, isn't a problem as the MS is restricted. Your countermeasures for clones was quite suitable, I'd say. Good use of making use of Sasuke's then snake summons. You lacked a bit in your Taijutsu rebuttal, as Sasuke did in-fact get outmaneuvered by Itachi at the beginning of the fight, and saying Sasuke wasn't serious at the time isn't really a counter at all, it sounds more like an excuse. Then you go off and claim Chidori Nagashi can dispatch of Itachi's clones. While he can potentially do so, that IS if all three of them go into ambush Sasuke, which I doubt. Also, Itachi's clone explosion trick could possibly resolve that. Since 1time hadn't properly countered it though, it's calm. You did however make up for the Taijutsu case, as the Cursed seal does increase his overall capabilities. You used Manda brilliantly, and I feel as if Itachi infact doesn't have enough if his arsenal to take it out of the picture,especially since Sasuke will be there, further pressuring Itachi. Let me close upby saying the body shedding exhausts a tremendous amount of chakra, using it would most likely hinder Sasuke's performance. He really used it as a last resort.
Winner: Draegod. I do feel as if the match-up was unfair though, Hebi Sasuke has the clear advantage, and without MS, he's extremely limited.