I'm not sure how making amends is accomplished by dragging him into a criminal enterprise. One that will add a future doctor to the organizations indebted payroll. And it's true that we don't have any clue how extensive Chucks past overlaps with Victoria's. I just don't think it will matter at all much beyond cliffhanger bait.Chuck isn't really messing with the MC as much as he seems to be trying to guide him and possibly make amends. He warns Kat about going too far with the Rose porno scene to the point of an implied threat to Kat about him being like family. As we don't quite know the history between Chuck and Victoria yet, we can't truly say what happened. Did Chuck sit in on one of Don's movie shoots and see Victoria? Was this before or after Ian and Edwin met? Maybe he saw her at a filming or in a movie and later met her as Ian's BF's mom/person Ian looked up to as a mother and helped her/convinced her to get away from doing porn. Until we know for sure what the past is between them we can only speculate.
TBF your overlooking the fact that this could be a catalyst for him helping/siding with Van Doren to take down the Club's leadership. We've already seen the in home meeting where VD warns him, maybe this could be the factor that pushes him to align with them to remove the current leadership. They have the resources and are already working on their plan. Remember it's not the club he would want revenge on it's the people responsible, taking Kat and Chuck(if he had a negative hand in Vic's past) out of the picture somehow (not killing but destroying their reputations/lives) would be a fitting revenge. You can add others along the way who are involved like Warren with Kat and maybe Grace with Chuck just to tie up other loose ends. This is all just speculation but if Edwin wants to get revenge on Kat and Chuck siding with VD would help him out immensely.
The option of helping VanD is certainly an option of one sort. It's a possible future solution to a now problem though.