Looking at how Kakashi treated Itachi in both their clashes, it seems he didn't respect him much.
First against him in the Hidden Leaf, Kakashi expected to handle him while his allies had their eyes closed. Then with Chiyo, he considered his chances for victory to be guranteed simply because of his teammates (Naruto and Sasuke) who had almost no teamwork experience in recent times. This despitehim acknowledging a knowledge disadvantage of massive proportions.
The thing is, as far as Kakashi knew, Itachi had defeated the entire Uchiha clan, with standout members like Fugaku among them. That's not just a single clan, but one of the strongest. While we know Itachi had help and that Fugaku didn't fight, Kakashi didn't know that. And he can't have thought of himself as some super powered guy as Naruto and Sakura were still in the action and at risk. So him working with them to take out Itachi (he didn't know it was a clone) suggests he thought that team was enough.
That then says that he either thinks such a team is enough to take out an entire clan or that he assumes Itachi had some major advantage. Accounting for the fact that it was never an open battle and Kakashi is not naive, he probably assumed that Itachi used stealth and strategy against them. In other words, he thought that an ambush provided the big advantage.
So Kakashi thinks an ambush (and maybe a little preparation) can allow one man to defeat a group that consists of hundreds of others that are similar to them.
Other cases of ambush being respected include the SPoP attack on the Hidden Leaf, Sasuke attacking Orochimaru and Kakashi himself. The SPoP attack, wherein they used a surprise tactic which implies that they didn't think a direct assault would be successful, had them expecting an ambush to give them an advantage over the most powerful organisation in the world. Sasuke expected an ambush to give him a win over Orochimaru who he later confessed would've trashed him if not sick and Suigetsu himself said the victory came down to opportunityand any of them (Team Hebi) could have taken out Orochimaru. Kakashi uses a tactic of sending out clones to evaluate an opponent and then rushing at them in a surprise attack. All these cases show ambush being a highly and openly respected tactic within the story, by characters with vast knowledge of battle and shinobi abilities.
So just how much of an advantage does a successful ambush give someone in battle?
First against him in the Hidden Leaf, Kakashi expected to handle him while his allies had their eyes closed. Then with Chiyo, he considered his chances for victory to be guranteed simply because of his teammates (Naruto and Sasuke) who had almost no teamwork experience in recent times. This despitehim acknowledging a knowledge disadvantage of massive proportions.
The thing is, as far as Kakashi knew, Itachi had defeated the entire Uchiha clan, with standout members like Fugaku among them. That's not just a single clan, but one of the strongest. While we know Itachi had help and that Fugaku didn't fight, Kakashi didn't know that. And he can't have thought of himself as some super powered guy as Naruto and Sakura were still in the action and at risk. So him working with them to take out Itachi (he didn't know it was a clone) suggests he thought that team was enough.
That then says that he either thinks such a team is enough to take out an entire clan or that he assumes Itachi had some major advantage. Accounting for the fact that it was never an open battle and Kakashi is not naive, he probably assumed that Itachi used stealth and strategy against them. In other words, he thought that an ambush provided the big advantage.
So Kakashi thinks an ambush (and maybe a little preparation) can allow one man to defeat a group that consists of hundreds of others that are similar to them.
Other cases of ambush being respected include the SPoP attack on the Hidden Leaf, Sasuke attacking Orochimaru and Kakashi himself. The SPoP attack, wherein they used a surprise tactic which implies that they didn't think a direct assault would be successful, had them expecting an ambush to give them an advantage over the most powerful organisation in the world. Sasuke expected an ambush to give him a win over Orochimaru who he later confessed would've trashed him if not sick and Suigetsu himself said the victory came down to opportunityand any of them (Team Hebi) could have taken out Orochimaru. Kakashi uses a tactic of sending out clones to evaluate an opponent and then rushing at them in a surprise attack. All these cases show ambush being a highly and openly respected tactic within the story, by characters with vast knowledge of battle and shinobi abilities.
So just how much of an advantage does a successful ambush give someone in battle?