I took some advice from my previous post, and after stepping away from the project, I finally came back to finish my Jolly Roger. I may make some minor adjustments to the hair, but I am trying not to be a perfectionist about it.
I'm no graphic designer, but I think it turned out okay. I still cannot draw a good skull myself, so I used a modified skull from Adobe Stock to get the look I wanted. Other than that, everything was made by hand in Illustrator after looking at various references.
The next step is to turn it into a real flag. I may go with a flag printing service at first just to have it, but I would like to eventually make it myself by hand sewing it together.