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The game doesn't always properly balance out the differences in players, leaving many not so good players with high demands and an AI willing to sign them to fill its needs.
This has been addressed somewhat, but probably won't be fully corrected anytime soon.
For the time being, I would do what Nutlaw said. It really is the only way. Since the game doesn't correctly ask for a realistic contract per every player, you either need to tweak the contracts or increase the money. You could put average ticket price or something like that up, but if you do nothing your teams will probably go broke and it really isn't a better way to play.
When I play OOTP, I take into account the limitations of the game when I set up my rules and options, with even more limitations coming from user made sets and mods. This basically equates to an unrealistic experience if you aim for realism and a slightly more realistic one if you tweak those realistic settings until you get something that might be less real, but make the game more real at the same time. If that makes any sense.
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