Those are some great thoughts straight from Jack's head. I still don't think it would be insurmountable for him, though.

Jack seems practical (pragmatic?) enough that he's learned (from Daniel, even) that sometimes you'll just never know the what ifs. He put charlie behind him, and that's chock full of we'll never knows, but lacking an opportunity to change anything, I think he'd accept his good fortune. (destiny? sorry, OTPd a little there)