Never is an awfully long time friend... Sometimes the small improvements are "just enough to tick all my boxes!" to justify higher and higher prices, and for many audio enthusiasts even $2000 headphones or headphone-based audio systems are major bargains compared to what you can get in the speaker world. The detail and 3D dimension of a great binaural recording played through a good DAC, amp, and headphones can seem more "real" than even a 9.1 speaker setup with height channels.
Or maybe they are planning ahead for "when" they win the lottery, or regularly saved money instead of buying lotto tickets and cigs and stuff. If it's your hobby, all sorts of price ranges become reasonable and justifiable.
If you don't feel like you can justify over $X for headphones, then go with that instinct. However, you may be surprised one day.
Yep. My speaker/amp/source system costs more than 2x of my Stax SR-009/SRM-272A, and although good I find that some of the factors you mentioned sound better on the Stax than in my speaker system.