Cory, I was listening to your recent livestream on a trip up to the Coop store today, and heard you talking about headsets digging into your head. I have always had this problem. I'll cut to the chase, you need a Sheepskin Aircraft Headset pad/cover. I have included two links to what I am talking about below, I do not endorse these particular stores in any way, just using them to show you what I am talking about. They are worth the money and your head will thank you. I would suggest finding one that allows you to velcro around your headset/headphones, as that allows for much easier on/off and swapping as desired. Some of them are designed to be slid on after removing an earpiece, much more permanent like, just do your research about how they go on before buying one. I know this because I bought the wrong ones first time. These will add some height to the headphones, but are super padded and feel like a cushion of air on your head.
https://www.aircraftspruce.com/pages/av/headsetx_headband/sheepskin11-12497.php
https://store.davidclark.com/sheepskin-head-pad-40592g-01
