S1: The only way Naruto can win in this scenario is to charge up a Flash Bijuu Dama and be able to successfully fire it. That won't happen when Hashirama's Mokuyryu and Mokujin (Physical strength on par with Full Kurama) are all up in Naruto's face. Due to the superior strength, and the chakra absorbing dragon, Hashirama beats Naruto in CQC. Naruto neither has the speed or capability to break away from Hashirama's Mokujin while using Kurama Mode, so he probably never gets Flash Bijuu Dama off. That doesn't include Hotei Hands spawning right next to him, or Flower Tree World's immense branches sprouting from below him....If Naruto can use Flash Bijuu Dama, then he wins. If not, he loses. Though he has a strong chance of victory here.
S2: Naruto might lose. No Bijuu Dama is a factor besides Flash Bijuu Dama since Mokujin would easily catch/repel any other Bijuu Dama Naruto has shown. If he stops to form a Flash Bijuu Dama, Hashirama drops a Gate right on his neck, or he just keeps Naruto in CQC with Mokujin and Mokuryu, which can match PS with a Senjutsu buff, and the normal Mokujin already rivals Full Kurama (>BSM Naruto) in physical power. PS is faster, stronger, etc. Mokujin is equal. And the size difference is immense, so he'd smack Naruto around giving him little to no time form a Bijuu Dama. Mokuryu also becomes many times larger, which it's full body dwarfing Bijuu Sized Juublings. Put that thing in CQC with Mokujin's help, and Naruto gets bound real quick.
