Yeah i would go with Sasuke and Oro too. Those two are both extremely smart and combined, would be more than enough of a match for Shika and Kakashi's smarts. Both Sasuke and Oro know how to use clones, regeneration, and Sasuke's Sharingan really well. Sasuke's Sharingan would outmatch Kakashi's in my opinion, even if Kakashi has a MS. Both Sasuke and Oro's Genjutsu abilities would out do Kakashi, and outlast him. Like one of you said, Sasuke and Oro have a larger Chakra amount than Kakashi, Shika, and Sakura. As for Sakura. Her strength will only get her so far with Sasuke and Oro's abilities to trick with genjutsu and clones.
I would also give this one to Sasuke and Oro.
As for Oro vs Kakashi, Gai, and Asuma. Nobody stated anything about Gai releasing his gates. With that, his Taijutsu, Kakashi's Ninjutsu and sharingan, and some help from Asuma. I think they would win.