at first glance i would say naruto loses them all, but on second thought, maybe not. current kakashi is sharingan less, so his ability is greatly reduced, putting him below SM naruto comfortably. but adding hebi sasuke to it may balance it out nicely. although this version has no ems, so no hax jutsu, but it does have curse seal. the curse mark is not on sage mode level, but it is a power boost. honestly, a clone can deal with kakashi, especially without sharingan. it will come done to if sage mode naruto can beat hebi sasuke. oi think thats an easy one, so naruto wins in the end. even though this version of sasuke uses karin, naruto is a close range fighter, and thus sasuke would risk killing himself. otherwise naruto takes this mid diff at most.
for the second scenario though, the outcome is much harder. war arc sage mode naruto is greatly improved over pain arc naruto, but can he take on 2 sharingan users at one time with it. what would give naruto a hard time here is sasuke's amaterasu. naruto takes out kakashi with a clone once again as war arc naruto clones were fighting kage level opponents and winning. naruto should be able to react to the amaterasu with his precog and superior reflexes. the other problem comes in the form of susano. if he can bust susano, he can win. we saw war arc naruto make a giant FRS, the one he threw at madara. if that hits sasuke's susano it most likely will break from it. plus sasuke can only keep susano on for a short while with only MS. can go either way.
naruto takes round 3.