If Jiraiya is part of this then Konoha's victory is assured.
Only Jiraya seems to be a threat here.. But whole village? Even itachi can't pull that off..
This as well.
The fact is, with Jiraiya they'll win pretty easily, sage Jiraiya IMO is close to, if not equal to Itachi. With the support of hundreds of shinobi (including the likes of Gai and Kakashi), Itachi wouldn't stand much of a chance. But Itachi could, as I'm sure someone will suggest, pull out susano to protect himself. The problem with that is although none of the shinobi could break through it, Itachi's weakest attribute is endurance; there is no way in hell that he could keep up susano long enough to wipe out Konoha. Jiraiya and Tsunade could bombard him with summons as well, as great as Itachi is he isn't winning this. You would have to take out Tsunade, Jiraiya, Gai and probably even Kakashi to make this close.
Read op it is not the whole village at the same time
Well if you had explained it better people wouldn't be making mistakes.
And it doesn't matter, 12 at a time? Jiraiya, Tsunade, Kakashi and Gai would be more than enough, the other 8 could go relax.