in the times that he's brought things onto himself by being a genuine asshole or gross pervert, i've not felt sorry for him. i don't feel sorry for him for losing megan, for example, because he was being creepy and weird.
but almost every other time, yeah, i empathize with him a little. the shit that bluespike did, getting manipulated by the idea guys, his house being set on fire, things like that. i think it's easy to feel bad for chris during most of the goings-on after bob died, specifically, since that was sort of the true beginning of his mental decline into insanity.