Hm, does losing to Bradley again affect crew respect or just area respect? It was actually pretty difficult for me to figure out how to get from -38 to -40 crew respect and I'm wondering if I missed opportunities to farm negative crew respect.
EDIT: Oh, I can still repeat it even though the dialogue makes no logical sense after defeating the Warlord. Still reduces area respect, but doesn't seem to change crew respect.
EDIT again: Seem to have hit the limit, though. I'm at -24 area respect and don't really know how to decrease it any more.