Let me put it a different way then.
Let's start with Chuck as he's the most "in the know" where Edwin is concerned.
Chuck knows what the MC's past is like because of Ian and his own personal interaction with him. If TD had omitted the rage, impulse control issues and violence, then putting the MC in an environment with the likes of Kathleen, Warren and August would be low risk. Your typical nerd wall flower that can be guided and groomed. If anything with regards to Chuck/Victoria comes out later, he's in a pretty good situation to smooth that over and, as you said, make amends. That isn't the case though.
Chuck took Edwin, as written, and put him in a den of predators and handed him on a platter to Kathleen. It's difficult to believe he doesn't understand what that could lead to. He set up a smart, educated and potentially vengeful person in a place that can much more easily unravel his previous facade of caring mentor.
Kathleen is most likely in the know about Edwin's past as well. Yet, she risks making him an enemy multiple times. Scratch Edwin's past and it makes sense that Kathleen wants to groom another pay date buddy. At worst, she gets one more person to torment. At best, she gets her new sidekick to validate her world view. All fine well and good as long as Edwin isn't a person that, not long ago, showed a willingness to get physical with no consideration of the consequences.
As for the now versus future problem. It became a now issue and not a tomorrow issue the second Kathleen dialed Victoria's number that first time. That is, if Edwin actually gives two shits about his mother. So, VanD's plan to one day take down the club is fine if you don't care that Chuck, Kathleen, August, Warren, Jacob etc. will target Victoria with violence if they get a whiff that Edwin plans to help VanD do what he is doing.