This occurred to me reading your story of the guy who barely made it through school. You know, telling the story from the guy's point of view might be more useful. Here he is, struggling with the system, and over time and with enough effort he manages to claw his way into a future that he's created for himself.
Same goes for the CEOs "ruining" the company. Get a new executive job, the board of directors are a bunch of idiots, nobody wants to take ownership and the ship is going to sink one way or another. So you keep the ship afloat as long as possible. Meanwhile, since you've managed to keep the company viable much longer than most others could, you get a nice reward.
I'm not saying that these people aren't morally defective in some way, only that you, as the author, are applying a moral judgment to the story that the reader needs to be aware of. I could tell these same stories much differently.
From my own personal experience, I find I understand systems well enough when I can assume that all players are acting in good faith and intelligently. I don't need dumb people at the bottom or sociopaths at the top. In fact, that's the irony of it all: once you begin to make moral judgments about the qualities of various people in systems, it becomes much easier to behave in ways that most folks would find offensive.
Just thought I'd point that out. Nice stories.