I think the confusion might be a combination of bad translation and missing novel details. Basically VTIC, in the original timeline, was unsuccessful, so Cheongryeo jumped off a building. He returned to the past with another chance to fix the group, but according to the status window, everytime he 'fails', he gets sent back to the beginning.
Considering he doesn't have a status window, meaning he doesn't even know the details of his missions (unlike Moondae who knows 'if I don't debut, I'll die') then we can assume that he died and returned multiple times (we can also assume that from his ghost story). But now that his status abnormality has deactivated, he can no longer return to the past.
When Moondae looked into his past with the truth check, one of the things Cheongryeo mentioned was that the member line-up was the fundamental cause of VTIC's failure (that's why Moondae brought up VTIC's final member line-up to him, basically saying 'I know you played a big role in that'). What Cheongryeo meant when he said he 'sent someone away' is that he literally tried to send one of the members away to their hometown because he knew they would leave VTIC after three years anyway to set up a company(?). In other words, there was a member who was going to cause a controversy in VTIC, and Cheongryeo 'failed' to send him away, so the system killed Cheongryeo and made him try again.
This
Wait, the long gaps between episodes is lowkey making me confused. What’s the deal with Cheongeryeo. I understand he must have died once but other than that, I have no fucking clue what he’s talking about.
What does he mean he tried to set someone back to their homeland and they ended up dead? Does that mean there were people like Moondae before? But why say homeland instead of timeline, different dimensions?
Does anyone have a grasp on his backstory or background that’s not including spoilers but just from what we know now?