I just went through transition about a year ago. I was at the Children's center in Detroit for 24 years and built up the biggest extended family ever. Transition was talked about for about 4 years, we just kept putting it off because we had such a great relationship and I didn't want to leave everyone. Finally I decided to transition. I now see a CF doc at the University of Michigan and I love it!
I have to say that transitioning was the absolute hardest time for me emotionally. If I would have left Children's when I was 17 or 18 it would have been easier, but since I waited so long I grew even closer to everyone at the hospital and that made it harder.
So I guess what would make it easier is to really encourage earlier transition and get adult CF docs involved early on in the transition phase.