I’m curious what phones you have found fall into the negative side of this?
I’m familiar with Audeze LCD-5 and 2c, and Abyss Diana, Sennheiser HD-800s, 800, and 660s. Currently using Meze 109 Pro, and looking at Arya.
I didn’t find any of the high-end phones uncomfortable. I didn’t like the Diana’s sound. The LCD-5 was super, but represented too big of an investment. The HD800s was fine, I wanted to experiment with planar headphones and found the LCD2c too heavy. I agree with the clamp force issue with the 660s. I couldn’t keep them on.