I doubt that Itachi is on the level of pre-time skip Kakashi.Defeating a sharingan user often had been mentioned at various part of the series:
--Hamper their vision (this seem to mostly work on lower level of Sharingan or people who got an implant) refer to Kakashi vs Zabuza.
This only works for Genjutsu. If gai applied this to his fight with Itachi he would have gotten Amaterasu in his ass in 2 seconds.--Gai had clearly shown at multiple times that Taijutsu was in general a good way to deal with most doujutsu users. Gai did even mention that he could close his eyes to fight him or just look at his feet when he encountered Itachi but then again Kakashi replied that only Gai had the specialization to do that.
lol... Only two ninjas together can defeat a sharingan user. Is Jiraya two niinjas?-- Chiyo apparently had encounter with Sharingan user before and talked about a clear way of fighting them.
When did that happen? Page?--Tsunade mentions to Kakashi that she was disappointed that he didn't manage to break out of MS on his own, which seems to be not as hard as people think but then again she was a sannin (Jiraiya is one too).
What Itachi have that we know about:He has shown to have kaiton against his fight with Sasuke. He most likely has another element and probably a third too. Also he is extremely intelligent and strategist. He has extreme handseal speed to the point that Kakashi failed to notice his seals.--MS
--Apparently able to make Illusion with his finger (see vs Naruto)
--Tremendous amount of speed (unless told otherwise he and Sasuke were pretty even)
-- Most likely has some Kaiton (Uchiha tradition to master fire)
I agree.What Jiraiya got:
--Bunch of frog Summon Jutsus (including Gamabunta)
--Various Taijutsus defenses (spiky hair refer to fight with orochimaru)
-- Bunch of Jutsus Kaiton most of them.
-- Adaptability (if his fight vs Pein wasn't proof enough that he could adapt to most fighting condition dunno what is)
--the cheap frog genjutsu
Neither has the toad jutsu. We have not seen Jiraya doing this jutsu against a proficient Uchiha user who has specialty in genjutsu.SusanOo and Frog genjutsu are both I WIN button. the frog genjutsu works against doujutsu user as proven by paralyzing Pein bodies without any difficulty. SusanOo is said to deflect every attacks but so far, the limit of this ability haven't been tested either.
Susanoo is a summon. Itachi does not have to concentrate imo. Jiraya has to wait to get into sage mode and has to wait for the toad jutsu. If Itachi wants to kill Jiraya with Susanoo he can try in less of 5 seconds.Their I WIN buttons are powerful but sadly having been manifested only once during the whole series, we can't really put a point to those. Does Itachi need to concentrate when he performs Susano'O, meaning constantly keeping a flow of chakra going because the frog genjutsu can simply make him stop. How long does Susano"O assuming Jiraiya managed to land his frog genjutsu and Itachi had his armor up...will Jiraiya have to wait it out for the armor to wear off?