I have my own personal boundary, but I'm generally unwilling to impose it on anyone else. If someone wants to be an asshole, I figure it's their call to live with the reward/consequence of their actions. Lots of people get shit, who "didn't deserve it." That's just how it is. If I'm in a position where I can help someone out, if I don't harbor a grudge against 'em, I'll consider it. Chris falls in neither category.
With that said, I think Chris is the most remarkable when he's not being controlled. That doesn't mean I don't like trolling, but outright blackmail isn't as interesting as setting up a situation before Chris and letting him come to his own decision how to handle it. Jack Thaddius flat out telling Chris to hump his PS3 for hours is amusing, but less interesting, than Liquid Chris presenting him with a rival and letting Chris do what he does.
I'm one of the least sympathetic folks here, in regards to Chris' plight. Despite this, I'm not here to relish in his suffering (I do, but it's not my primary motivation by a longshot). But, even if that was my motivation, I just don't see any need to manufacture grief for Chris. So many factors, over several decades, have naturally come together to write the lamentable story of the Chandler Clan. Grief is almost inevitable in that house, even if nobody else in the universe had any influence over them.