This isn't really a solution so much as a tip as a solution for achieving all achievements in a game is kind of pointless. I had one last achievement to obtain and that was the "Mailbox Full" achievement for getting 500 messages. I unlocked the "Mailbox Full" achievement but the "One More For The Road" achievement would not pop after 10 minutes. I went back to the dashboard, quit out of the game and loaded up again, went back into Career and it popped right away. So if you are having a problem with it not popping, give that a shot. Maybe that's a fix for it or maybe I just needed to wait a tad longer but thought it would be a good tip if it may not pop for someone. Cheers!