I've seen two different schools of thought and I'm struggling with this a lot myself.
Say in TBL I have a 33 year old (or MSL I have a 35 year old).
They want a four or five year contract. You know that will take them way past the years of useful, but you also don't want to lose them right now.
You can give the big contract and hope they retire... or you can let them walk.
Are they more likely to NOT retire if they have a contract with years left on it? Anything like that? Notice any patterns?
I've always been more conservative and let the player walk. What say you? What's your logic or thinking behind it?