My friend wasn't afraid of flying either, but one time, he was overseas and when he stepped on the plane...out he went, fainted dead away and it's taken him about 10 years to get to the point of being able to get on a plane w/o fainting. It took a lot therapy to help him. It also took a lot of people telling him to go see a doctor or don't talk about it again.
Yes, it would be far easier to find a job closer to home or keep the travel to a minimum, but he isn't ready to listen to you or anyone else. It's going to take a serious health issue for him to see the light and change his business lifestyle and I don't see that happening in the near future.
I hear you...you are getting tired of hearing about his problems. They will wear you down if you allow them to.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
