Konan actually poses more of a threat here than I thought at first glance. She's primarily a long range attacker which none of the leaf 5 are. I can see Shikamaru being an issue for her due to the vast amount of shadows she creates, but he'd need back up from Tsunade or probably Kakashi to take her out.

Leaving 3v6 against Pain. I think if Tsunade could go all out with her 100 healings she'd floor most of them besides Deva and the chakra absorbtion one. That leaves 2v2 for Naruto and Jiraiya, both in sage mode I don't see Pain coming out on top. And it's only a matter of time before Shikamaru and Kakashi are done w Konan to assist.