You are certainly improving, proportions much better.

As Scott says wetting the quills before tying will make them softer. They are the same material as your finger nails. They get soft when soaked in water...
Also holding the quill in hackle pliers makes things easier. I like to use a pair with BOTH a spring and swivel for the job. They stop twist and jerking. They are hard to find though. You'll easily find one of these features, but not both. There is a cheat you can use though. Get a fine rubber band (size 12 is ideal) and tie it to your hackle pliers. When you wind the quill hold on to the rubber band. It will cushion the quill while you wind it.