New to this whole thing...
But how about an advisor (who sends updates to your inbox) who's in charge of monitoring the happiness of your contract year players?
He'd tell you if your player was happy with their current playing time, their position, the ballpark, their slot in the batting order, their coaching, etc. Then you could make adjustments if keeping him is a priority.
Examples:
Boss,
I recently got off the phone with Goody "He Hate Me" Morizone. As you know, he's up for free agency next year. He tells me he's unhappy with the amount of at-bats you're giving him. I told him that we're all for one and one for all... but the line went dead.
What to do?
Thomas Mockery
Big Man,
Who do you love? I just got off the phone with Goody "He Hate Me" Morizone. He couldn't be more thrilled with the organization. I floated the idea of him playing here into the future and he didn't object. He said that the organization knows how much he's worth and if they fork it over, he sees himself staying in Buffalo for a while.
Thomas Mockery
Thoughts?