Was Kakashi being hypocritical in supporting Shikamaru's revenge?
The short answer is: no. Shikamaru was actually after justice, not revenge. But I'll get to that later.
I saw this take before, so I'm starting with this: was Kakashi against Sasuke's revenge?
When Sasuke says his famous line of "there's someone I've sworn to kill", this is Kakashi's reaction:
He does not seem particularly happy about this, but he doesn't say anything. Kakashi expected it; he knew Sasuke was after revenge. It was something he accepted and even used to encourage Sasuke, as seen here:
He's telling Sasuke not to give in to hatred, telling him to keep a cool head to achieve his goal. Again, I don't think Kakashi seems happy about this, but he isn't discouraging Sasuke yet.
Then comes the Sasuke versus Naruto incident. When Kakashi breaks up the fight, this is his reaction:
So far, Sasuke was indeed a broody kid, but he wasn't consumed by hatred yet. He willingly disboyed Kakashi's orders in the bell test to give Naruto his food, and he also willingly sacrificed himself to save Naruto from Haku.
So far, Kakashi knew Sasuke as a grumpy kid, but he didn't think he would be capable of trying to kill one of his friends. When Gaara intrudes their training, this is how it goes:
This is what Kakashi says:
Up to this point, Kakashi didn't believe that Sasuke was full of hatred. Tht was why he taught him the Chidori.
He trusted Sasuke not to use this beyond an actual battle. I do think is indeed a too strong technique to teach Sasuke, as I didn't think Kakashi intended him to go through a path of killing his opponents. But we have to remember that he was going to face Gaara in the Chuunin last exam. It was the best shot Sasuke had to defeat him.
So Kakashi was disappointed when Sasuke used the chidori against Naruto:
When Jiraya asks about it, this is what Kakashi answers:
So far, Sasuke and Naruto showed a healthy rivalry. Kakashi encouraged it, as he knew both kids wanted to prove themselves to each other. And we must remember that Kakashi's experience with rivalry is between he and Gai. Arguably, they both have the only healthy rivalry in the entire manga.
But Kakashi acknowledge that Sasuke was acting like this because of Itachi:
That's the moment Kakashi decides to intervene. Up to that point, he accepted and probably intended to help Sasuke with his revenge against Itachi. But he noticed Sasuke was full of hate, and him attacking one of his teammates was where he crossed the line.
This is his face when he tells Sasuke to give up. He's not angry, he's sad. He probably knows what this means to Sasuke, but he also knows that he can't support this anymore.
In here, he makes it clear that the Chidori is not supposed to be used against his friends and allies:
Lastly, he tries to appeal to the Sasuke he knows: the one that cares about his teammates:
I do belive that, if it weren't for Orochimaru's interference, Sasuke might have listened. He seemed deeply affected by Kakashi's words. But shit happens.
About Shikamaru's revenge
I don't think it was revenge. Shikamaru was bringing justice to his deceased sensei. He wasn't lost to hate. And he wasn't doing it alone. He trusted his teamamtes to go along with him. It was a joint effort.
This is what he says when Tsunade acuses him of seeking revenge:
To Shikamaru, this was duty. He felt like the battle was left unfinished. He wanted to end it.
Those are Shikamaru's last words to Hidan:
In my opinion, he's not full of hatred, as it would be in the case of revenge. Shikamaru is following the Will of Fire and fighting to protect his village and the memory of his sensei.
As for Kakashi, this is what he says to convince Tsunade to let Team 10 go after the Akatsuki:
Many say that Kakashi "learned his lesson" with Sasuke and changed his approach with the revenge thing, but I disagree. I think that's what Kakashi inteded to do for Sasuke. Things weren't supposed to go so quickly, he wasn't expecting Sasuke to meet Itachi again so soon. They didn't know yet what Akatsuki purpose was, and weren't expecting them to try to kidnap Naruto.
Sasuke and Shikamaru weren't the first people Kakashi saw seeking revenge/justice. He already knew they couldn't be stopped. He just changed his approach with Sasuke because he was turning against his own comrades.
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