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Since plot no jutsu has a bearing here, the winner will also be decided by "Plot no jutsu" only. Guessing wouldn't be correct coz we're not sure about the plot itself. Only a few battles in naruto have been decided by the match ups, rest have been decided by plot no jutsu anyway

Naruto becoming the 10 tails host, having it well under control, finally ending with Naruto and Konohamaru inventing an array of sexy jutsus

Great, I'd like that student be son of Sasuke, the sensei being Konohamaru. Finally Konohamaru introducing Naruto as THE GOD OF SHINOBI. Just like IRUKA introduced the 3rd as the strongest in the village

yes if it's a basic one. We've seen him break out of it during chunin exams and in the fight with sound ninja. He definitely has smarts for that