Did Kakashi eventually surpass Itachi, Jiraiya, Tsunade, and Orochimaru?
Taijutsu

Jiraiya got the Frog Kumite, Tsunade has brutal strength, so it is clear here that in terms of Taijutsu, Kakashi is not as strong as those two. As for Orochimaru and Itachi, they don't use taijutsu much so it can be said that Kakashi could be on the same level or better.

Ninjutsu

Kakashi is the renowned Copy Ninja, the one who has copied over 1.000 jutsus. In term of Jutsu knowledge, it can be said he is on par with Orochimaru if not greater. Tsunade is not that great in ninjutsu other that ninjutsu for healing purposes. Jiraiya has great ninjutsus but if we talk about the jutsu element, Kakashi can perform 4 basic elements (Katon: Goukaku, Suiton: Suiryuudan, Doton: Doryuuheki, Raiton: Raikiri). He was also able to learn Rasengan, which was rated as an A rank jutsu. Meaning that it is very hard to learn. Itachi, being an Uchiha, would be able to copy jutsu the same way Kakashi did. So they can be said on the same level. However, it is not known whether Itachi can use 4 elements like Kakashi did. Itachi for sure can use fire jutsus as demonstrated during his fight against Sasuke. Kakashi learned to use Susano'o after Obito transferred his remaining chakra to him upon his death. So here, Kakashi can be said has surpassed the other 4 in this.

Chakra

Kakashi is very well known as having a low reserves of chakra. He commented that Naruto has about 4 times of his. And considering that Naruto-Sasuke-Sakura was like the new Sannin of Konoha, it can be said that Jiraiya has about the same or greater level of chakra than Naruto. Orochimaru as we know is a chakra monster, same with Tsunade. Itachi is pretty much on the same level as Kakashi in term of chakra reserves, except that being an Uchiha, he gets less strain than Kakashi in using the Sharingan.

Genjutsu

Kakashi is better in Genjutsu than Jiraiya, except of course, when Jiraiya used the help of Fukasaku and his wife (the frog sennins) to cast sound genjutsu. He should be better than Tsunade and Orochimaru too since he has the Sharingan. He, however, is far weaker than Itachi.

Based on this, we can say that overall, Kakashi hasn't surpassed the other 4. He's just pretty much on the same level, or a bit under the other 4.