That’s the tough part. Knowing themselves very well makes the decision easier. While DS would go anywhere, DD doesn’t even want to take her car to school 45 minutes away because she is nervous to drive on the highway. She would never go out of state.
Ever since DS was little, we had him lead the way in airports, pick out transportation routes and let him weigh in on how he would handle any of the travel delays and disasters we’ve faced. This was child-led as we knew there would be no stopping him once he got older and we wanted him to be prepared. We did not have DD do the same. They are different kids. He was ready to take on the world and she was much more cautious. It was only recently that DD and I got stuck in an airport together and I made her figure out what we should do, just to prove to her she could do it and so that she wouldn’t experience anything like that for the first time while traveling alone (although she isn’t the type to want to travel alone). Perhaps on your visits you can have her take the lead a bit to see how she feels about having to make those types of decisions and to be there as back up before she possibly has to do it on her own.