I believe in both scenarios neither are destroyed completely, especially Rhaast. When Kayn wins, Rhaast is forced in a dormant state, like a coma. He loses his concious, and waits for his second taxe to consume Kayn. When Rhaast wins, Kayn loses his body's control and switches places with Rhaast in the weapon, sweeping in oblivion (where Rhaast is).
Eventually, if Kayn continues to use the darkin weapon, Rhaast will always be the winner, no matter what. When Kayn dies, Rhaast consumes the body anyway. When Shadow Assassin occurs, Rhaast still has the chance to wake up and show himself again. When Kayn loses though, it is over. His soul is not destroyed but destined in a far worse state, trapped in oblivion until end of time (or darkin weapon's magic being removed/weapon is destroyed).
It is what I think.