Yeah...with full intel already at his disposal thanks to Jiraiya's sacrifice.
Jiraiya did it on the fly without knowing a shread of information about Pain. Jiraiya beating 3-4 Pains is a MUCH greater accomplishment than Naruto defeating all of them.
They are. Just because Orochimaru lost to Uchihas doesn't make him a loser. Jiraiya, unfortunately, wouldn't last long against Itachi either.