I always like to remember that they were playing a highly advanced alien video game, so it's fun to think or headcanon that there were pre-programmed things set into the game to sort of kick off certain routes/endings. Like, when you play a game and you kill off an NPC that's important, you will inevitably be put onto a different route than the one you were on before.

I think the multiple deaths may be staged in this repetitive way not only because our characters are stuck in an actual cycle of violence, but also because the game can't think of any other way to have them die legitimately due to the role they were assigned when they first started.

Their session of Sburb was also weird and abnormal. Perhaps the Scratch and resetting everything also fucked with how they died multiple times as well, which would cause problems down the line. If Sburb is a game that takes time travel into account due to their being Time players, then I'd say the moment they started the game probably "glitched" because it already knew they'd have to die a lot to reach their end goal.