People never seen to acknowledge that there are two sides to a negotiation around here. Everyone always wants to be the GM and not the player agent.
If you're Jimmy Howard you probably tell the team that you'll negotiate for a couple months and then if we can't work something out, then I'll be playing the market after the season. If you're the player you can't just wait and see how the season plays out because then you might lose your leverage.
Holland kind of is over a barrel here because of its not Howard, then who will it be? Rinne just signed. Bobrovsky seems too rich for our blood. Do you want Mike Smith or Cam Talbot? Varlamov? Do you roll with a lesser quality guy and give the starting job to Bernier? You can't put yourself in a position where you have to give up assets for a goaltender at this point in your rebuild.
If you wait too long on Howard and he has a nice season, I'm sure he'd rather go play on another team closer to contending. Calgary, Edmonton, Colorado, etc.