While Kakashi was making his way to track down members of Akatsuki, They were busy making plans of their own. With the recent losses of Hidan and Kakuzu they decided to make a more active push to get the rest of the tailed beasts. Their recent movement were how Konaha was able to get any information.
The good news about this is that Akatsuki would be divided so in a worst case scenario Kakashi would only have to fight against 2 at once (although with their ego, goading them in to 1 on 1 fights should be easy). The bad news is this could make them harder to find. Since the best he could do was chase rumors, Kakashi wouldn't even know who he would be up against until he got there. With the thinning out of Akatsuki's ranks, that left the possibilities as: Itachi, Kisame, Pain, Konan, Zetsu, and Tobi(Madara).
As luck, or possibly bad luck, would have it, the first ones he had managed to track down were Itachi and Kisame. Thanks to Kakashi's dogs, he had advanced notice and was able to stop before encountering them and come up with a plan.
Even at 20ft, attacking them head on presented a significant risk. On the other hand, he could use his modified version of the new jutsu to try and drain their strength in a sneak attack. The downside of that is he could be discovered, allowing them to get the first attack in, or he could be successful and get even bigger which would make it harder to sneak around tracking the rest of Akatsuki.
Either plan had the potential to work or fail about equally, so weighing the consequences Kakashi decided on the best course of action.
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