I looked through an encyclopedia thingy for star wars and it didn't mention anything about his fear of flying, so I'm guessing it's not supposed to register as a plot point?

" Obi-Wan was taken from his family at a ery early age, once his affinity with the Force was evident. Note that the novelization of Return of the Jedi claims Obi-Wan was the first son of a moderately wealthy family, and he was a fast learner. He sailed through his education at the Academy, and was praised by his family as well as his acquaintances in the Old Republic"

Maybe they, err, flew him away from his family?


..you can tell that I've loved star wars all my life, can't you.