My roommate is basically a walking HR lib who generally thinks things are as good as they can get, will always side with ownership in any hypothetical, and whos personality largely tevolves around explaining why bad things are actually good. The rope thing is dead on, rather than alienate her with constant confrontation I use questions and framing to steer her in directions where that contrarian urge can be useful. Sometimes she'll repeat my own points to me a week later as if they were her own, and I always respond "shit, that's a good point."