The headphones thing is very much a matter of morphology and personal preference. I know for instance anything other than IEMs is intolerable over any significant period of time for myself.
And choice of headphone! Open versus closed headphones lie much different on your head; clamp strength and weight vary hugely as well. I'm on my third set of AKG k702s as the only headphones I can wear for hours; finding the right pair for anyone takes time.
The most comfortable headphones I have are my open ear Hifiman He-400i. Minimal clamping pressure, and they’re more breathable due to being open backed. I can wear them for hours without issue. The downside is that they only work if you can get away with open backed headphones. They’re useless if sound leak is an issue or if you’re on an airplane or something. But for working at home in my office by myself they’re ideal. And they sound way better than anything else I’ve tried.
This is true. I had a leg up when I chose my setup, because I've been active in the headphone hi-fi community for a few decades and had a collection of various cans and some knowledge of what I was looking for. My WFH setup uses Beyerdynamic DT880s, which are generally known for being comfortable with low clamping pressure, minimal weight, and because they are open tend to not cause ear sweat as bad as some other options.
Absolutely. I'm a fan of the SteelSeries Arctis 5, but the wireless version (Arctis 7) has too much clamp strength to be comfortable for me. Sony's WH-1000XM4 is a good wireless option on the go, but because it uses bluetooth it murders the quality of incoming audio if you use the mic.
It's a series of tradeoffs, and finding a headphone that is right for you and your situation is far from trivial.
