Obstacles yes, insurmountable no.

If an existing celebrity pilot like Angelina Jolie offered to become Young Eagles chairperson, you would get a good size bump in the press coverage for a week.

If a non-pilot like Taylor Swift or Scotty McCreery agreed to learn how to fly with the help of EAA, over the course of six to twelve months (because of their hectic touring schedule and time commitments, ahem), then you would get a huge bump in press coverage for... wait for it... six to twelve months