Spoiler:
The way I see it, the Third was above all of the Sannin in terms of skill at that particular time. The problem was that he had aged so far that he was unable to utilize that skill properly. His age had made him frail, and his chakra capacity was lower than what it had once been. Orochimaru even admitted to some extent that if the Third had been maybe 10 years younger he could have defeated him. So I think that both Jiraiya and Tsunade at their current maximum would fall just short of the Third in his prime.
As for Naruto and the Kyuubi chakra...He will probably never have the ability to use it liberally. The red chakra is an extremely volatile double-edged sword. I won't say why unless you ask (or happen to already know), but in the second half it becomes very unwise for him to use that chakra.
At the time of the exam I would guess that he is above the average Chuunin due to the Kyuubi chakra. The thing is that he has that explosive Summoning technique that could put him above those who don't have the raw power or technique to deal with it (or the speed/initiative to stop him from summoning). The case is sorta the same with Gaara. I could see him beating Chuunin at that time, but could not honestly see him going toe-to-toe with a Jounin. Gai, for instance, was easily able to deal with Gaara's sand. But the moment that he unlocked Shukaku the situation changed completely. However, Sasuke was originally able to stop Shukaku's summoning by taking the initiative and piercing Gaara's 'impenetrable defense.'
Kakashi is not as strong as a Sannin though. He has many limitations due to his bloodline incompatibility with the Sharingan, and his overall chakra is probably only somewhat above average. He is a genius ninja though, and quite young. He could surpass a Sannin in time, but at this point he lacks the battle experience. He is still weaker than Itachi, who is also not Sannin level. Itachi himself stated that if he and Kisame fought Jiraiya (a Sannin) head on, the best case scenario would be them killing Jiraiya in the process of him killing them. More men would not change the outcome of this. So while Itachi outclasses most Jounin by far, he is not yet of Sannin level.
The Sannin are not necessarily stronger than Hokage level though. The thing is that the Hokage level fluctuates. It is the term for the strongest ninja in Konoha, while Sannin refers to Jiraiya, Tsunade, and Orochimaru specifically. The Third and Fourth were probably as strong as Sannin, and in the case of the 3rd had exceeded that of a Sannin thus far while in his prime. But basically, you could just say that, right now, Hokage level and Sannin level are the same thing, especially since the Fifth is one of the Sannin.
And Akatsuki...It's sorta hard to say when we don't even know who the leader is. I would venture to say that most known members are about as strong as Itachi in their own way, if not slightly stronger (though not in the realm of a Sannin). I assume that Orochimaru is at a big disadvantage right now, effectively lowering his level. This is one reason why he is at a great disadvantage to Akatsuki. I won't explain the reason unless you want to know, though, even if it's rather simple. The other reason is Akatsuki's sheer numbers, but that would be less of a problem if Orochimaru was in his prime.
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