For players that are willing to sign extensions during the season, will the contract that they are willing to sign change throughout the season? Starting from spring training to the playoffs, is the contract they are willing to sign the same all year?  If that's the case, there's no reason to sign them until the end of the season to protect yourself from devastating injuries, right?

Do you ever give those extensions, or do you wait until after the world rolls over?

No, the offer won't change during the season.  You're right, there's no real reason to sign him early in the year, wait it out.

Depends on the player.  If he's a 29 year old  with great makeup, I'll sign him during the season.  If he's a 33 year old who is already declining, I'd wait until after roll over to see his ratings.  You could sign a guy that looks good during season X then he might lose 3-5 points in the offseason... and that will **** you off

Sometimes a player won't resign if you wait until after roll over.  I agree though, consider the player's age, makeup and current rate of decline.

Thanks, very helpful.