how to do everything optimally.
Everything is not supposed to be perfect. Do you understand that you are trying to implement a bailout button. If the game get's a bit hard, use it. People learn by making mistakes and living with the consequences. Smarter guys read the forums and rules first and try to learn from other peoples mistakes.
Ok let's say new players get in trouble. They actually start looking for answers and write in the forums. That is exactly what we need, don't you agree? Tutoring them how to manage the situation is exactly what it should be about. I'm pretty sure many of them just bought some players have no left over cash, but still want to add players. They are impatient and think they have made the biggest mistake. Everything takes time in this game. This should be their first lesson. Without those managers coming in the forums, they will just use the reset button, spend the money again and with one reset used still come to the forum for help or just quits. Nothing really changes.
Even having negative balance in divV or divIV and all bad players, you can salvage a team selling/retireing all bad players, releasing staff, earning profit for a few weeks, getting some players for 1-10k transfer fee and still win games against bots. This can be done in less than 6 weeks. I guarantee you. What you need is forums and reading some game rules, if that takes a team near bankruptcy for a manager to do it, then better late than never. No amount of resets (atleast not that one) will help him to understand what he did wrong and how to avoid it in the future.