My ex lives two states away and he flies up to get my 8yr DD and then flies back with her. This has been happening since she was 3.
She is not confident (despite him trying to make her feel guilty about the cost) to fly on her own.

My situation is a little different in that he is deliberately unemployed so he doesn't have to pay me child support. So my ultimatum is if he wants to see her he can get himself here and get her back.

When DD is confident enough I won't mind letting her go alone but I think five is too young. What happens if she needs to go to the loo on the plane and needs help? or uncharacteristically gets upset and has an unsympathetic hostess, so she then develops anxiety about plane travel? Too many what ifs for me.