Is it possible that the island is messing with Jack in a false future? Perhaps it is manipulating Jack to get him on board about staying on the Island.

Because Jack has a more rational personality, the island knows it can't manipulate him with visions the same way it would Eko, Locke, or Desmond. It had to implant a false future as a cry for help to get Jack to want to stay.

Think about why Jack's ex-wife shows up as an emergency contact in the middle of the night. Jack didn't have a life threatening injury. It doesn't make sense unless this is a vision that reinforces for Jack why his life sucks back in the real world. I mean, why would she leave her house and show up?