Team 2 is
obito prime, madara, onoki, mu, danzo, shisui, kakashi, kabuto
If Shisui's genjutsu is allowed then team 2 stomps.
Even without it, I don't see team 1 winning here. Kabuto in sage mode alone would likely be enough to keep Itachi occupied (especially with his techniques that attack the senses), plus Shisui could reinforce him, since he'll have a good understanding of Itachi's fighting style.
That leaves Hashirama to face Madara (who alone would give Hashi a fight), an opponent who he can barely lay a hit on (Obito), Kakashi, two dust-style users and an izanagi spammer (Danzo). Even with his sage mode and uber summon I doubt Hashirama could pull out a win. Though this team lacks the firepower of the Kurama/Madara combo, they'd outnumber him 6 to 1 and four of them can one-shot/BFR him.
Team 2 win, with or without Shisui's genjutsu.
Director David O Russel and Crew do the Hustle in a baroque comedic farce with some real humanity to it.