I'd love to know what has to go wrong in a man's life that they're still harbouring such childish revenge fantasies in their forties. There are plenty of fat, burnout losers out there, but I've seen few as maliciously bitter as Bob Chipman.
Nothing has to "go wrong"
As much as nothing "goes right"
My own experience with tender misanthropes/narcissists like Bob is that they can have a steady job, a roof over their head, and enough money left over to indulge in a hobby on the side.... but STILL be constantly angry they don't have MORE, attributing their lack of "success" not to having just not worked hard enough or having had a few unlucky breaks, but, that society is not rewarding them enough for their (self obvious) superiority, if not maliciously plotting to keep them "down".
If it's an apartment, they deserved a house, if it's a house, they deserved a mansion, if it's a mansion, they deserved one in a better neighborhood..... and on it goes.
They always think they've been slighted, somehow..... it's where an overly-antagonistic worldview always leads..... to the point where you can find a $5 bill on the ground and curse the world for not giving you a $20....You or I would see winning the lotto as a once-in-a-lifetime windfall. Bob sees it as his destiny that has been denied day after day after day. And even if he did win, it wouldn't make him happy since having been forced to wait so long for it means feelings of "why should I just be happy that someone else finally did their job?!! Where were you 20 years ago? I missed my chances at greatness because I didn't have money, all because YOU didn't give it to me!!!!!!" would overwhelm the occasion.
What we see as revenge fantasy on 40-year old slights best forgotten? Bob sees as finally correcting an error that not only caused injustice then, but continues to this very day.
The way you or I would feel if we woke up to find our car stolen? That's how Bob feels every day he looks outside in the driveway and sees a Ford instead of Ferrari.
The levels of anger and frustration are exactly the same.
Except we only feel it when we seem to have been singled out for misfortune, Bob feels it constantly as he is denied what he sees as his just rewards.... In fact, he may even be less angry at the theft because that would validate his view that the world is out to get him, whereas owning a white-bread car that reliably humms along for 10 years would only prove he's "average" like the rest of us.
TL : DR - Life to an average person is large swaths of normalcy punctuated by occasional good fortune. To the Bobbos of the world, life is constant disappointment, punctuated by moments of being given only what barely passes as "good enough".