Kakashi can use 20 Riakers-10 MS-and his nin dogs all he wants-and he can use his other elemental justu's 6 a fight.
Fight 1-Asuma and Kuriana
Fight 2-Itachi (no MS or Genjsutu)
Fight 3-Hidan (Kakashi nows his technique)
Last Fight-Naruto(KN2 higst) Sai and Sakura.
Dont say Naruto past Kakashi we all now he hasent.
I think he can go through it all what about you.
Fight 1
Asuma and Kuranai never stood a chance against Kakashi. He has intelligence, speed and strength, and they have no gates. Kakashi can do better jutsu than them, and Kuranai's Genjutsu is not as good as Kakashi's. The way I see it, Kakashi will send in some clones. Kuranai will try a Genjutsu, and while she is performing it, Kakashi can use his Mangekyou Sharingan to transport either the majority of her body or her head to another dimension, leaving only Asuma against the Kakashi clone and Kakashi. Kakashi, who is still concealed, can now pull out another Mangekyou Sharingan and also Raikiri. I'd say that the Shadow Clone would probably use Multi Shadow Clone jutsu and attack Asuma, getting him cornered into an area where Kakashi's Mangekyou Sharingan implosion attack will be able to go from behind Asuma and transport a vital part of him away. If that doesn't work, he'll surely lose at least a limb, after which Kakashi can pull out another one or two implosion attacks and rip out the remaining limbs if not Asuma's head. Once that is done, Asuma won't be able to dodge a Raikiri and will die.
Winner: Kakashi
Fight 2
Genjutsu and the Mangekyou Sharingan may be the main things that Itachi uses to battle, but he is extremely powerful with out it as well. When he fought with Kakashi in Episode 80 of the anime, Kakashi commented that he could not even see Itachi's hand seals. Combined with Itachi's clever attacks and strong jutsus, I say that normally he'd win. His speed is so much greater than Kakashi's that trying the implosion would be an idiot's move, so all that gives Kakashi an edge is Raikiri. But Itachi is too fast, his reflexes too quick, and also remember that he doesn't have a Mangekyou Sharingan, but he does have a Sharingan, which will help even more to prevent him getting hit by Raikiri. So I'd say he would win, but it depends on how much hiding space and rock there is around him (Kakashi does well around rock). He should win anywhere shown on the series so far, but a rocky and leafy area is advantageous to Kakashi.
Winner: Itachi
Fight 3
No questions asked. If Shikamaru could do it, Kakashi definitely can.
Winner: Kakashi
Fight 4
Limitting Naruto to KN2 makes things more interesting. He would obliterate Kakashi with KN3 or KN4. As it is, Kakashi will be hard pressed to win against KN2.
Against people of Naruto and Kakashi's calibre, Sai and especially Sakura aren't much. This is probably the best plan of action. I'd say that Sai draws some creatures to attack Kakashi will hiding somewhere reasonably far away from the fight, with a set of paper clones to draw more monsters to attack Kakashi. While Kakashi is busy with the paper creatures, Sakura clocks Kakashi on the head as powerfully as possible, probably revealing him to be some kind of clone. In the meanwhile, Naruto is charging up KN2 and Kakashi's main objective would probably be to try and kill him before he reaches it.
At this point he'll probably be normal KN (not KN1, he hasn't yet achieved a full tail of power). Kakashi would probably use his implosion technique to get as close to him as possible, and then rip his body away with as many Mangekyou's as it takes. Possibly 3 or so. Kakashi then goes out into the open with his real body, and performs the Multi Shadow Clone jutsu. He then uses his dogs to sniff out Sai, and then an Earth contol jutsu to completely solidify the rocks around Sai so that they compress him with bone-crushing force, thus killing him. I don't think Sakura's much of an enemy; Kakashi will probably use Pakkun to find her quickly, and then kill her using comparatively incredible speed and a Raikiri.
If, however, Kakashi missed with his Mangekyou implosion attack, or Sai's paper got in the way, or something that allowed Naruto to go to KN2, then it would be different. Kakashi's aim is not improved by his being able to use an extra large amount of Raikiris and implosion attacks; KN2 will probably defeat him on its own. If not, Sai's paper barrage and Sakura super-strength will finish the job.
Winner: Dependent
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On the whole, I know that Kakashi is powerful, but I doubt he could handle the entire exercise.