http://oi48.tinypic.com/2mfassk.jpg
Direct answer. Written by Masashi Kishimoto himself.
That does not mean the made-up thing you think it does.
Itachi knew almost everything about Obito and
still thought he needed the EMS to compete. However, that panel shows that Itachi died never knowing how powerful Obito
really was.
Itachi's trap caught Obito
off-guard... and it
still failed; as Itachi expected it would and
that's why he left the crow with Naruto.
Obito wasn't even talking about a confrontation with Itachi, he was talking about Itachi's trap possibly being successful
if he knew more about Obito; purely a hypothetical conjecture based on no feats.
And the end of the day, Itachi believed Obito to be a weakened Madara and knew almost everything about him, yet never once in 10 years lifted a finger to stop Obito because he knew he
couldn't.
Now stop trying to troll.