Itachi; if kakashi did surpass itachi it isn't until the late war arc. plot says passively activated sharingan you lose chakra, something kakashi always made sure was closed until needed where as itachi was known to keep his active as long as possible. something only uchiha's could be able to do due to their inherited slight lowered cost to use dojutsu. Lastly, itachi illness likely lowered his stamina yet managed to sustain susanoo, amat, tsuku,clones and katon throughout the fight. Databook stats only applies to base meaning no sharingan involved. So even if kakashi would have better stamina than sick itachi doesn't mean he has the neccessary stamina to handle as much dojutsu as itachi unless the stat gap is large(which it isn't)