If Naruto has to start out in base form then he probably looses as he'll have trouble with his clones pretty much being fodder while he tries to gather SM, and Kazuma could probably get to him before it's complete. If he starts out in SM, it all depends. Can he in the fight in five minutes or not. And with Kazuma's willpower to keep going I don't think he can, and Naruto won't have the clones to back-up his SM.
So either way he looses but if he starts out in SM I think he'll have the upperhand until he's no longer able to use it. And I highly doubt Kazuma would give him any reason to go tailed-mode. Or at least above 3, which he can control himself. But SM > 3-tails.