If You Don't Fall In Love, You'll Die - Chapter 53

In a world fraught with innumerable dangers where living day by day is a struggle, a young man from the modern age transmigrated into such a world, accompanied by a peculiar system made for assassination.

When Simon dies, it turns out there's more to combat than lightning reflexes with his controller, and the path to becoming a hero is more brutal than he can imagine as he descends into The Pit. Death after Death is a dark, time loop/Isesaki story with roguelike elements, that explores some of the common tropes in a different light.

Cao Gui: “Well said! System, but do you want to explain why this is not Marineford but Manhattan in New York?”

System: “…”

Cao Gui: “System?”

System: “…”

Cao Gui: “System, say something!”

- Description from Novelupdates