Finally, I don't think yours situations are the same like Borislav's situations
Borislav's team is not the team on the line. He just hate to lose a fellow BB player. Just pointing out that he is not crying for his own sick mother.
In competitive leagues you often have to balance around the 0$ mark to stay in division. Some time it could happen that the circumstances makes a team go into bankruptcy even if the manager tries to avoid it (but also trying to evade relegation). If the manager does not take action in due time, (because of commitment to the players, league, whatever), he should still not be sent packing. It is disheartening at the very least to get all of your players listed at the same time, on top of that in a low market would be the utter destruction of a team and the managers spirits. You could argue that he buy and sells in the same market, but his players listed at 0$ probably goes below their value, and the correct concoction of players takes a lot of time to put together. Also, the right player only comes along every now and then.
Perhaps an option could be to give teams more time with age. For instance (starting with the best paid players)
1. season - all the team listed
2. season - 3/4 the team listed
3. season - half the team listed
4. season - 1/3 the team listed
5-7. seasons - 2 players listed
8+ seasons - 1 player listed
This would reflect their die hard fan base developed over years and years with blood sweat and tears, and the enterprises credibility with the bank. Thinking that managers are unable to change is an adamant approach. Perhaps they have been in an economical unbalance, but they may actually have attained enough experience to prevent it happening again.
If they go bancrupt again they are treated as the step above, increasing the consequences if they don't take action.