Yep, it was quite a challenge the first time. I watched the video that came with it again right before loading it and that helped. I had to think for a moment when I was doing the backing to make sure I was putting it on the right way.
It would be so much better with two people, one on each end, to keep the top and backing rolling straight. I would do a partial turn, walk to one side and straighten, walk to the other side and straighten... back and forth.