Thanks guys. I'm gonna keep trying to convince him that the bike isn't worth the time/money/effort and her should get a nice used mountain bike to commute on.

I kinda figured the chain line was a large factor in the way the rear of the bike was malfunctioning.

I kinda figured wheelsets would be mentioned. I'll look into a set but I think that'll exceed his budget... Maybe it'll convince him to just get a better bike