Perhaps a more aggressive stance should be taken by the AI - right now you get the warning that you have contracts that are about to expire, but this has two problems: 1) sometimes you do want to let the contracts expire, and so you don't want to be bothered with that message after every sim because you're done, and 2) if an owner is not logging in or is just ignoring it, all their players go to free agency. (I tried to time it where if you don't log in during the time that the warning would show then you lose the team at the end of the season and the AI re-signs everyone, so it's probably more of a problem of owners not seeing and/or ignoring the warning)
What if, instead of the way it works now, as you near the end of the season you get a warning like this:
You have players who are in the last year of their contract and must be re-signed in order to continue to be on your team. If you do not offer a contract to these players before the end of the season, the AI will attempt to sign them for you. If you are not interested in re-signing these players, [click here] to clear this message for the rest of this season.
You would have the ability to close the message like you can now, which would cause it to appear again after the next sim if you still have unsigned players, as it does now. But if you were to click on the link to clear the message for the rest of the season, the message would not be displayed again and the AI would not re-sign any players to an extension. Essentially it still would give you the same control you have now but the default would be to have everyone get re-signed unless you knowingly were letting your player contracts expire.
Thoughts?