I would hurt all of the whumpers just to see their reaction tbh.
I would help Diamond and Sugar.
In the JB universe, a lot of the whumpers, especially the Jeweler, wouldn't exactly know why you were hurting them, because in their minds, they aren't doing anything wrong.
Diamond would very much like any and all help you could give to them, even though they're a pathetic, useless thing that can't help anyone.
Sugar would be reluctant to accept any help, but once he knew your intentions were kind and pure, he'd be very grateful and try to show you that.