Interesting thread. If I can weigh in here about Head-Fi and headphone enthusiasts.
First, headphones have not yet seen the drastic and unprecedented rise in prices seen in speaker-based systems. The most expensive, at least regular production models, run around $6K. Try that on for size on speakers alone. I remember when I first became involved with audio systems in the early 1980s. I also remember when I thought an Infinity IRS system costing $50K was outlandish. I just saw a pair of $1.1 million speakers for sale used for $432K here on Audiogon.
Second, I agree that headphones have made more inroads into the younger generations. Maybe not the most expensive tier but just witness the number of younger folks listening to headphones, perhaps to drown out all the destructive noise in our society.
Third, I am probably guilty of riding the incessant merry-go-round of sonic improvements where equipment is most important and music merely test software. It really is all about the music and whenever I enter that realm I am much more happy and relaxed than when I am obsessed with sonic upgrades.
Thank you.