What really bothered me about Jack's angst was Cas and Bobby not pointing out to him that the Winchesters by and large don't have powers, a few seasons excepted, and yet they've managed to save the world. Telling Jack his powers will grow back doesn't seem as useful as pointing out that the guys he emulates don't have powers and do okay.

Also, I would give someone my firstborn and put up with ALL the demon drama if it involved the demons deciding Sam is the king of hell and showing up all the time to bother him with questions about the way it's run.