Chris will give up once his main cheerleaders--Barb and Anna--either kick the bucket or somehow vanish from his life. I know Barb isn't doing much to help his situation now, but the long-term effects of her incessant coddling are undeniable. And, even though Chris and Barb's relationship is more strained than it used to be, it's still going to be a difficult adjustment without having his mother's unconditional...love (if you can even call it love?) in his life.
Anna, I think, is going to be the most insidious person in terms of making sure Chris never quite 'gives up', for better or for worse. Even when Barb passes and Chris gets even a vague glimpse of the future ahead, Anna will always be there, telling him that the future will be peachy and the people who don't get you can go screw themselves. All of this truly makes me wonder whether Anna will decide to stay in the picture long after Barb is gone...normally, I wouldn't see her falling out of cyberspace since she gets so much gratification from asspatting Chris, but what else more is there going to be of Chris once Barb passes? What will happen to what is probably the most meaningful relationship outside of his family, no matter how toxic it is to his well-being, when Anna decides she's milked him for all he's worth? Then what? ...Or will it somehow work the opposite way and Chris will see the light and sever his connections with Anna? But will he still give up when he sees the incredible damage he's done to his health, to others, and to his overall quality of life?
I mean--I really don't know. In one respect, I still want to think he has some faint modicum of hope that's being strung along by the fact he's not completely isolated (yet), but on the other...looking at his newest selfie tells me he may have already given up.