Brahmsian
500+ Head-Fier
you see people who have scored the TOTL gear and beyond still unsatisfied
Often it's not so much that they're unsatisfied so much as that they're audiophiles--that is, they love audio gear as much as or even more than the music. In that case, there's really no reason to stop trying out new gear, particularly in your example where the person has unlimited funds. As long as they're into the hobby, they'll naturally be interested in listening to new gear. Having said that, there might also be an element of dissatisfaction that helps drive them toward trying out more and more gear.
People can also become dissatisfied when they don't take headphones on their own terms and want them to sound like speakers. It will lead them toward one headphone after another but they will never be satisfied, not even with the TOTL.
I don't consider myself an audiophile. I'm more about the music. Basically, I'm just interested in trying out a few headphones and seeing which two or three I like best (ideally two open ones for home use and one closed for when I need to keep the music in or out). I've already found two open ones I like very much. I'm curious about a few more. Then hopefully I'll be satisfied for a while before I start looking at headphones again.
Of course, there's also the phenomenon where you start turning into an audiophile slowly, over time, without even realizing it.
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