Major respect for trying something outside your comfort zone @infamy! You did really well. But I have some fresh advice that I think you will like: Let’s forget sculpting!
I was trying to figure out how to phrase my feedback and couldn’t. The fact is this would be much simpler to use cloth simulation to get right: Let Blender do the work for us!

I will demonstrate this today during the casual stream. Look for it live or in the recording 👍