You are being far too optimistic here, and I'll tell you why: Does Chris look mentally fit at all to wake up and say, "Hey, both of my parents are dead, maybe I should be a lot more serious about my finances since I don't have a job?"
He'll do the same thing he always does. Wake up midday, spend almost all of his newly freed dollars on video games and junk food, ramble about some inane delusional shit on social media, and roll around in his own filth, until he loses everything. This is if he is left to his own devices and doesn't have a caretaker or his family doesn't step in.
Let's face it: Barb taught Chris all of the wrong lessons in life, and now that Bob is gone, there is nothing to separate the wheat from the chaff when it comes to Chris' well-being. Chris is doomed barring some sudden epiphany that he's a colossal fuck-up and he changes himself for the better.