Itachi can easily beat Tsunade and Orochimaru. Since Pains attacks isn't that effective against Orochimaru since Orochimaru can take hell of a beating,and physical attacks is almost useless . Genjutsu is the best method to beat Orochimaru, as proven.
Pain beats Jiraiya. Itachi beats tsunade and Orochimaru. And it can even be Pain beats Tsunade and Orochimaru, And Itachi beats Jiraiya.
And plz dont bring up that Itachi said he's a stalemate to Jiraiya. Kisame even knew ITachi could kill him. Thats why Kisame said" Why is a retreat necessary for you"? ANd Kisame admitted Itachi can handle jiraiya, but he couldn't himself. Itachi doubted himself, just because Jiraiya was called a "Legendary Sanin". Which proves NOTHING, since Itachi owned A Sanin in 10 seconds. And Kabuto owned a Sanin too. So Itachi contradicted himself for nothing. When he's already proven otherwise.
So you should compare techniques, not entirely what someone said. Thats like saying Raikage wud lose to Ino just because Raikage said" he's a stalemate". No. You have to compare their techniques/intelligence/stats, not just their mouth.
And Pain can definatly beat atleast 2 Sanins. Bansho Tensei wud easily take out Tsunade. And pain has an almost indestructible body, SO Jiraiya's attacks are almost useless against Deva, only Tsunade wud be capable of crushing Deva path, and she is too slow. And wont have any openings with Itachi by his side. And pain has Shinra Tensei.
If push comes to shove, he also has Chibaku Tensei, but Itachi wud have to get out of range, so he wont get caught.
So Pain beats Jiraiya/Tsunade since he's more of a physical fighter, and Itachi beats Orochimaru because Itachi's Genjutsu is ESSENTIAL, so that Orochimaru wont get a chance to use Edo tensei, cuz if Oro uses Edo tensei, then Sanins win. But luckily Itachi Genjutsu disable all of Orochimaru's Techniques, since you can't do anything inside of his Genjutsu, which was already proven with Orochimaru before.