I don't think things are looking up for Jack at the moment in the flash forwards, it is confusing guessing where each fast forward falls in the timeline of events. But if It plays out the way I think it will, Jack is headed toward a downward spiral. He starts pill popping, lashing out, and his ability to communicate with other people decays. I just think he's either too proud like his father, or chickenhearted to go to Kate's house. and maybe after a long time of putting this visit off Kate decides he's not worth it anymore. (hence the anger shown toward him by her in the last episode of season 3.)

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" We kinda like knew that forever ago." -Hurley SE4EP8