Just one of the duo can solo in my opinion. Maybe if Obito had both Sharingan or Juubito mode for the fight he can win based on Naruto's rust though, but that's subjective.
Same as Kenshi said. Even pre-Rikudo Naruto ought to solo apart from perhaps Obito via hax. If we include Juubito, I doubt it'd change much for Part 3 Naruto/Sasuke soloing the group with ease.