Not sure if that helps, but I experienced the same thing (reported it as a bug, now it's listed under "Known issues"), and so far I came to the conclusion that the bug depends on WHERE you try to wing up.
I tried to wing up with a fellow CMDR in HIP 60953 and in the surrounding systems, and I had the same problems you have for two weeks. Then we decided to move to Imperial Space (roughly 300 ly away near Grebegus) in solo play and after a while we tried again to wing up - it worked at once and over the course of several sessions, so I suggest you should try the same - I know it sounds strange, but it worked for us.
Best of luck for you - I know how annoying this issue is...