Tate no Yuusha no Nariagari - Chapter 295 - Sibling Fight

Growing up in a place where the rule of the jungle is law, the simple yet cunning Shaar is thrown into the chaotic world of war and political turbulence. After a chance meeting with a mysterious young girl, his destiny is forever changed as he embarks on a journey, joining the Byzantine army and climbing its ranks. With his bizarre beauty standards, will he ever return the affection of the girls that will follow him? Will he ever learn about his real parents? What lies ahead of him is a journey of strange humor and adventure.

An RPG gamer who played the realistic VRMMORPG ‘The Amber Sword’ for years, finds himself teleported to a parallel world that resembled the game greatly. He takes on the body of an NPC who was fated to die, and with the feelings of the dying NPC and his own heartrending events in the game, he sets out to change the fate of a kingdom that was doomed to tragedy.

- Description from novelupdates

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.