This Life, I Will Be the Protagonist - Chapter 657: Divine Game – Chaotic Blocks 48

After all, transmigrators of this era were no simple matter. Some became slimes, others turned into treasure chest monsters, and some were even reduced to mere skull--such things were all commonplace.It was nothing more than playing a villain, Shiayar didn't care. Wasn't it only natural to pay some price to become stronger?[Destined Great Villain System][“Let this world feel the agony!”][Newcomer Mission: Let the young and naive Grand Duke's daughter of the Azure Garden Dukedom, Miss Silvia, experience the betrayal of her loved ones and, amidst the pain and despair, complete her transformation and rebirth.]

Damian, a Centurion of the Punishment Unit of the Baroque Kingdom. “Damn it.” Just once. If I were given just one more chance… ‘I would have truly conquered the battlefield with these guys.’ At the age of 30, he closed his eyes on a nameless battlefield. But when he opened them, he found himself back 17 years in the past. And this time, he had a perfectly functioning mana core that could wield magic. ‘This time.’ I will rise higher than anyone else. I won’t be swept away by the turbulent times. ‘I will conquer.’ Damian, who has returned to the past, wields his spear toward the world.

The scum’s or villain’s long road of transformation was tentatively set to the world:
The abandonment of the educated youth’s wife (Completed)
The hidden marriage of the scum film emperor (Completed)
The best brother in the world (Completed)
The Phoenix male who destroy the bridge after crossing the river (Completed)
The treasonous general (Completed)
I’m an honest man (Completed)
To become the top scorer in the School of Agriculture (Completed)
The soft rice man’s self-cultivation (Completed)
The whole world is reborn (Completed)
I want to survive on a desert island (Completed)
The stallion male who has seized the opportunity (Completed)
The perverted self-salvation (Completed)
The spring of the loafer (Completed)
The misplaced life (Completed)
The miser career (Completed)
The ghost is out of feeling (Completed)
The Queen’s favorite husband (Completed)
The vicious girl with her godfather (Completed)
I want to be a good person (Completed)
I does not tear up the family (Completed)
The perverted common plant (Completed)
The Mary Sue’s men (Completed)
Every time I was reborn, someone wants to kill me (Completed)
The old people’s counterattack path (Completed)
The global evolution (Completed)
When I became a net red (Completed)
For you, good person (Completed)
His heart had white moonlight (Completed)

- 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.