There is a fan fiction which almost totally describes this. It's based in a prison, where the Winchesters do brief stint and the prisoners talk about them later. It's beautiful (Wincest, so if that floats your boat).
he was a neglectful father (Canon. Who leaves a small child for weeks at a time and makes them responsible for their sibling? They made illusions to abuse (Dark Side of the Moon, for one), and the boys have a lot of emotional issues stemming from this.
And then sam gets a dog Then sam almost dies Then sam gets possessed Then Charlie dies Then Dean dies Then Dean turns into an demon Then death dies Then Mary comes back Then Kelly cline dies Then Crowley dies Then cas dies But it's so good I promise