Itachi graduated from the academy at age 7, and became chunnin at age 10
Orochimaru graduated from the academy at age 6.
yep kakashi grad age was the youngest, but at 13 kakashi was just becoming a jounin and itachi was an anbu captain, i know kakashi was an anbu but never a captain.
and kakashi wouldn't beat oro
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oro: "Also... you were going to kill me...? Why don't you try? If you can, that is..."
Kakashi: "Ugh.. compete with him..? Am I... An idiot...?"
it looks like he even imagined fighting oro and thought he'd lose his head.
might be a little differnt if he straight out used kamui on oro's head, but he'd probably just grow a new one back the way he recovers lol.
on topic: i think sasuke would tie with kakashi as far as taijutsu and lightning even tho sasuke has made more variations of chidori like spear, current, senbons, but kakashi has the long range lightning dog and i think a weaker version of the spear.
Overall sasuke would probably have to use susanoo or amaterasu, kakashi would only win if he could kamui sasuke's head off before he used susanoo to protect him otherwise the MS drawback he has would leave him as a sitting duck to get sealed or burned.