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You know, what really kills my willing suspension of disbelief is that in all these countless loops (judging by the amount of bodies at the bottom of the cliff), apparently, they never got the idea to TAKE OUT THE HOUNDS FIRST before Guwon ? Of course, there is the possibility that they actually did and even succeeded, but then something else went wrong, causing a new loop. There are so many ways this could go, like Jinwoo choosing Guwon at the end and the rest of the towns people turning on him, pushing both off the cliff together (that would still require dead Hounds though). Anyway, I feel like the Hounds somehow hold the key to breaking out of the loop, hence the title of the story.
OK, Guwon has to be aware of the looping in some capacity. His words to Jinwoo the last chapters he was still alive HEAVILY imply it ("To me, dying isn't that big of a deal", "You've already tried to kill me several times, haven't you ?"). Also, he seems to be aware that the cliff matters ? He literally begged Jinwoo to take him up the hill despite being on the brink of death. His resoning for this was pretty shabby too.
And not just those recent chapters either. Guwon suddenly being there preventing Jinwoo from cutting himself in the kitchen in the middle of the night in chapter 31 is pretty suspicious too. That couldn't just have been intuition.
I think Guwon just remembered about the loop thing when he was about to die. at the beginning of the story, he has an amnesia, so I think every reset, he forgets everything.