99Joelegg
Yes that is a common problem without sunglasses never mind with them.
many headsets are clampers and I am sure cut off the blood supply around that portion of your head.
Add the metal from the sunglasses????
I always used DCs and found them uncomfortable after a short time then I changed to Bose and never looked back. I know they are expensive but change to Bose.
I have used Bose in both twin props and jets that I fly. You can wear them all day without discomfort.
The other ones which have been good are the very small telex. They are suitable and used extensively in jets but not sure how good they would be in piston props.
Pace