Here is Treadle Lady's video showing how to wind it and she also shows how you can bypass the little thing that winds it on and let your fingers guide the thread.
http://www.youtube.com/user/TreadleL.../8/GOu4-CG8RMU
Even with my new machine I sometimes have to "bump" the thread a little bit while it's winding onto the bobbin to get it all the way over to one side.