Don't worry I was also under the impression that Dulan wasn't that bad of a guy when I first read. I also blame the spoilers I saw that played down the involvement Dulan has in her suffering....
Yeah idk how Raymond did it. For his sake I want to believe that Raymond didn't last much longer than Karen in most of the resets. In a lot of them other than the ones where they got married and she just died the next day it seemed like his issues were the same or got worse. I can imagine him getting killed by Evans or the Marquis right after Karen in some instances. Thinking of him living to be an old man every time is just too sad
So, way back when season 2 ended, I mentioned that Ray was probably over 400 yrs old. Since what I understood at the time was that he only remembered the lives from the point of Karen getting pushed by Dulan onwards. But NO, he remembers ALL of Karen's repetitions, even AFTER she's died.
So let's do some math. Karen began regressing at age 17, after that, she repeated the same year 100 times. When the manhwa begins, she states she's turning 117, meaning she's on her 100th regression. She then dies by getting pushed off the towar by Dulan, and regresses a further 4-5 times before the current time we're on. This means she's around 122-123 yrs old.
Ray, on the other hand, lived for longer in each of those regressions. It's not disclosed how much in each but he states that he once lived to his 70s. So, let's say he's lived an average of 50yrs per regression and he remembers ALL of the 104-105 regressions (123 minus de 17 natural years of Karen's life that weren't regressions).
My man is approximately 6,100yrs old. Unstable probably doesn't begin to cover it.
On another note, I'm also the dummy that once wrote a dissertation on Dulan not being the bad guy. Obviously I was wrong, and I'd like to blame the reddit novel spoilers I read. THAT SAID, there's still shit regarding Dulan that hasn't been revealed. Such as him supposedly pushing Karen off the tower on purpose knowing that it would lead to Ray starting to remember. Why would he do that? Also, apparently he does repent in the end, not that it would matter in my opinion, the damage is done. But yeah, questions still need answering in regards to Dulan.