Well, I'm less convinced that people can't avoid trouble. As a computer programmer myself, I'm consistently surprised by how "creatively ignorant" users can be. I think the Manage My Team page's "Typical Weekly Net Income", while a nice convenience for me and other power-users, is the sort of thing that will mislead the users that otherwise wouldn't be clever enough to calculate it on their own. They'll see that number at +$2000 / wk or so and shortsightedly assume they're fine, when really over the course of a full season, they're deeply in the red if they're an average US D.III or D.IV team finishing 3rd, 4th, 5th, 7th or 8th with a short cup run. It's a newbie trap. Team bankruptcy isn't a prominent issue -- every team I've seen bankrupt is toting around some $300k monster C in a low league -- but I can't speak to how often people have to experience the unpleasantness of cutting roster just because they finished 5th.
As a serious suggestion for a very simple fix, why not have players unpaid during the offseason? Then the Weekly Income isn't potentially misleading, and Coco wouldn't feel compelled to churn his roster. I don't think offseason pay adds anything GOOD to the game. The main choice it gives to the player is between angrily writing paychecks for nothing for weeks, or selling guys off into a market that would become oversaturated as soon as more people realize they can and probably should do the same thing. Everybody loses?
After this point I went on a huge tangent about other economic aspects of the game, so I deleted that to focus on the issue at hand
Edit: I see Naker stole my idea!! kidding, kidding