I have made several winding ways quilts and have done them all by machine without a problem. They were all die cut, however. Here's one:
http://www.quiltingboard.com/picture...s-t198142.html
Also, I have the book: "Winding Ways Quilts: A Practically Pinless Approach"
https://www.amazon.com/Winding-Ways-...s=winding+ways
she gives tips on pressing that make the block lay flat, and her technique really is almost pinless. You can get a used copy pretty reasonably priced. She also has a lot of interesting setting options. Worthwhile if you are going to make more.