Sasuke will manage to take out all paths except Deva and Preta at most, but will be defeated due to him not having any counters against Chibaku Tensei (that we've seen so far)
Maybe, But maybe not. Because Naruto was able to relate more to Pain, and Naruto used up pretty much all of his chakra just to beat him. You'd need very high endurance to beat pain. But i'm sure he would come close, if not he'd beat him.
Well, the chances of him surviving would be 45 percent as naruto had to use two clones who were charging up for sage mode and beat only 5 bodies(paths of pain) out of 6. and my answer defiantly no. not ever,even with his team.
his Susano'o would get absorbed and his Amatersu would get repeled with Shinra Tensei and since he would have no knowledge on how to defeat the six paths of pain he be screwed and if it was just Nagato he be ****ed even worse