Dynasty Rebirth Infinity

What would you do if you reincarnated with your memories intact? That was a situation that Ewan, once a common and unassuming Serf, experienced too many times. Using his growingly vast life experience, he uses it to build himself and his descendants up in this harsh world, creating a dynasty he calls his own. As for how to achieve it? Why not see and find out? What to expect: A simple game-like system everyone has, Many Time Skips, MC death(Sometimes gruesomely), Death of loved ones(Sometimes also in a horrifying way or just dying of old age), Fast-Paced with several lifetimes, smut focusing on passing on the family line, and an MC who becomes increasingly darker with each death as he survives the darkness and unfairness of his cruel world.