Doing my own little Lost rewatch since I bought the DVDs I've been going through season 2 and after rewatching 'The Long Con' again, it hit me. When Hurley gives Sayid the Tailies walkie talkie to fix Sayid prevails at the end of the episode. They manage to get a radio signal and music starts to play, Sayid says that the signal 'Could be from anywhere' and Hurley adds 'or any time'. They look at each other, then Hurley says he was kidding.
Makes me wonder if maybe all along that everything before season 5 happened AFTER the events in season 5? Theories? I know there's plenty of holes, but still, this is my first blog so don't tear me apart.