Itachi and Sasuke - both of them have never failed to analyze anything. Kakashi utterly failed with complete Kamui analysis, which Sakura did so in a heart beat. It took him 200 chapters to replicate her feat. So, he he isn't in their league.
But that doesn't mean he isn't smart. The guy is still a prodigy and is a mulch-faceted Ninja. He is apt at using traps, tailing ninjas, and coming up with strategies. However, not even he is at Sasuke's caliber when it comes to quick silver strategies. The guy just dishes them out on the spot, in the face of death even. As that would be the time when it would be impossible to think straight.
I'll say, it's something like this:
- Itachi and Sasuke.
- Kakashi - though he is damn close.
Obito is not in their league.