Headset and shades combination
Hi 99jolegg,
I would suggest getting your sun glasses sorted first.
Go to a good optician with a decent range rather than a pilot shop. Tell the optician you want to wear the sunglasses under a pilot's headset. Look for some with a thin metal frame. An optician will also be able to exchange the earpiece arm cover pads, either for thinner ones, or for extra soft silicone-rubber ones. They may also be willing to bend the arms for you to follow the sides of your head.
Then attend to your headset. I agree the Bose is superb; I have a pair (because I'm a fanatic,) but they do cost a fortune. You do not need to spend that sort of money. Go somewhere where there is a good range of different manufacturers' headsets. Again, in view of the fact that you have had a problem, I would suggest going to a specialist supplier rather than a pilot shop. Look in the magazines to find them.
On choosing a new headset, aggree with the supplier that you should be permitted to take your new headset home and wear it around the house for a couple of hours. If it proves painful you can then return it and try another.
Good luck!
Broomstick.