I don't generally give the neighborhood much consideration during a daytime ride, aside from traffic issues, of course. The expection to that is the North Shore Trail (on the far side of the Casino). That trail creeps me out, and I try to avoid it. The vegetation grows too close to the trail, and there are too few visual clues to when/where the next bail point might be. Several times I've had people (innocently) step onto the trail right in front of me, and had no chance of seeing them through the leaves. As far as trails go, pristine is good, remote just doesn't work for me.
As for other areas, it depends mostly on time of day, and the speed I expect to be traveling as I pass through. I don't want to spend lot of time being the subject of scrutiny as I pass by. Mostly because I want to avoid the verbal badgering, which is about the worst I've encountered.