Agreed 100%. At one point Rachel/Tim are like joking and high fiving with the rapist prison guard and it felt so gross to me. They also have Boyd relate to him and let him go in S5? It seemed like they wanted us to see the guard as a pitiable character but it only made me uncomfortable.
Honestly, quite a few moments in S5/S6 where Raylan or Boyd pressure Ava make me uncomfortable in the context of Ava being a victim of domestic violence for a long time. But at least I feel the writers understand that and are doing it on purpose.