Chris seems to be as close as he's ever been to figuring out that he needs to make vast attempts to improve his life and that he's to blame for it.
He's never, not once, ever decided that he is in the wrong, or that he NEEDS TO CHANGE. The odds of this doing much are low on its own, but the rest of Chris' life is a long time and he's got many years of this ahead. Chris, though, has been here at least and made no changes.
The difference this time is that Chris doesn't really have an answer (even a bad or fake answer) as to what he can do or find his friends. Sonichu was, frankly, enough of a success that Chris COULD have made a better life on its production (think on that. If he'd embraced the ADs and used them with his own website, he'd probably be in the black. He did enough to get our attention as well.) But he's given up on Sonichu, and he's not been spamming contests (which some people actually manage to do and win).
So he dreamt of his High School Reunion. This was unrealistic from the very beginning, but he's either alienated his gal-pals entirely by his complete stupidity, or he misunderstood their relationship even then. In either case, there is no heading back into a happy high school--if it ever existed. There may be more trying to appeal to them, more lying and deluding on facebook, but the damage is mostly done and barring a trolling attempt on that exact point--Chris' Reunion Saga has devolved into this self-pity misery.
There are five things that are going to plausibly happen in CWC's future, but ordering them is going to be quite hard.
-Barb Dies.
-14 Branchland is greatly damaged/made unlivable.
-Chris gets in serious trouble with the law.
-Kick the Autistic
-Chris has a medical emergency.
Everyone has talked about

dying in the imminent future, but I think that's at least two years off. Barb doesn't seem to have mortal problems and her issues must be at an annoyance level if she's not interested in making any changes to avoid them.
14 Branchland is in no greater danger than any other house in its neighborhood for Hurricanes, Blizzards, etc. Despite the hoard, the house is probably at lower risk of having a fire (No cooking, for starters) than the average house. But there is a frontier forest in the front lawn, the paint has discolored at minimum. 14 Branchland probably has a few years before it suffers major structural damage through neglect as well.
Chris getting in serious legal trouble--this will come out of the blue, and its happened before. Chris is, to be fair, opposed to getting in trouble with the law on it own and would probably either run away from enforcement or quite possibly plead out ala 10/28/11. But he hasn't stopped doing stupid stuff that might land him trouble with the law, as the defacement of HEXbox merchandise indicates.
Although he's creepy, unable to understand boundaries between people and a mild dark person for his great ego and greed, Chris isn't likely to get his ass kicked. He's too much of a coward to interact with a "fan" at a McDonalds, so short of a run in with a robber of some kind (and would a robber even TRY to go after some threadbare guy with obvious mental issues?) Chris gets his ass kicked when he himself tries anything physical against even an average male, or when he is at the wrong place at the wrong time.
Chris has been on anti-cholesterol medication in his 20s and his habits are far from healthy or even the mildly dysfunctional conditions of the average American (IE, overweight, too little exercise, too much fat/cheap sugars in diet, etc). Chris' immediate family doesn't seem unusually vulnerable to medical issues, but Chris is pushing the envelope on low quality fast food and lack of exercise. Chris' mental health may well be directly tied towards his subpar physical state--and the relationship is a proven fact. Chris' habitat isn't that far away from an animal in a circus cage, too small a space for too long a time and too little to do.
Chris potentially could have a heart attack right now.
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Of the five, I'd probably think another brush with the law or a medical emergency is most likely to happen next--and neither will likely happen in 2014 itself. But in five years time, at least one of the five will happen.
This sort of grim forecasting means that CWC hasn't hit rock bottom--Yet. That awaits.