It does seem specification is needed. That picture of Sasuke is really vague. I believe he wore that up until the Sound Four Arc, which is a long stretch of time in which he became progressively better.
Kakashi hands down, he has more experience, had a better sensei, and is an all-round bad ass, while sasuke at kid age only looked good because all the other shinobi his age were shit.
depends...there are multiple factors and various variables to consider, not to mention the condtions in which the fight takes place in and blah blah blah whatever Im drunk