If Jack is an outsider, maybe he was never meant to be on the plane and/or survive the crash. Thats why he wasn't on Jacobs list
Yes, exactly. But now that he's there, what I took away from his line "That's what they say. That's not what they mean" about his tatoos is "I may be an outsider, but I am still going to join you where you live, at Home". He may still have an agenda about escaping, but I think when Juliet said "Ben calls it Home" he finally realized *that's* where Ben was going to take him, Home, not back to Los Angeles or wherever. He and Juliet will be the marked Outsiders when they all return Home, but I think Jack is cool with that. That's what I got from this episode re: Jack: an acceptance of his fate, his purpose; he's a leader, a great man, but that he's let lonlieness, fear and anger deter him from that path. He will be able to pursue that path with Ben and The Others.
I'd love it if, when we see Jack again, he's not all "vein popping, screaming" Jack but simply a doctor in Otherville, part of Them.