to make the pattern, you would cut one or more slashes from the draped hip to opposite shoulder, and spread the pattern several inches. It looks like they did both front and back this way. Try it in cheap fabric first...
Make sure the machine is threaded correctly, and the needle is set the right way; on my kenmore, the flat part of the needle goes to the back, and you thread from front to back.
be sure the bobbin is put in the right way. I hold the bobbin in my right hand with the thread trailing over the top away from me, then put it in the bobbin case held in my left hand.
For the bobbin winder, have you oiled it? Also play with how far in you press the lever; mine needs to be just a bit out from all the way in. Alternatively, you may need to reset or replace the rubber drive belt that makes the winder spin.