I do think about Cobes' future a lot, the Dark Lord's unfortunate but inevitable demise.
I think it's unlikely he'll outlive his father and step-mother. Daddy dearests seems to be a really fit guy and I wouldn't be surprised if he lived beyond eighty or even ninety years old (especially thinking how medicine is likely to improve as he approaches an older age). If Cobes continues how he is now but doesn't pick up anything harder like heroine, then I can imagine him living to maybe his forties or fifties, eventually the alcoholism is going to catch up with him and he'll die of heart failure. If he did outlive his father then he'd kill himself.
I wish your video wasn't just joking about him watching Cuties and him being a prison bitch or whatever. The New Vegas soundtrack and dialogue of all the Casperites' dismal but probable demise could've been really good. Not to be too serious but I do think about this a lot.