WE are supposed to believe that everyone involved in the show ,at least on Lucy's team , was born in the 80s after 83. So far they haven't traveled to any time past this date in the show. As for the older pilot, are we sure he was in the episode in 1969? I have only seen him in a relative few episodes and I don't remember him in that episode in the past. Maybe he used someone else to pilot the ship. They really haven't dug too much into Flynn's team and only recently discovered that the first female pilot was living in the 1800's. OF course this might be told to them as a way to keep them from interacting with their younger selves that might create a paradox. Like in Time Cop, where if you touch your younger self, you end up dead and wiped out of existence.