It's no different or stranger than people going to different restaurants to see how each chef prepares a dish. I like to order fried rice at least once at every Chinese restaurant I go to, because I like to taste the different variations of the same dish and each one is different than the fried rice that my parents would make. My wife does the same with French fries, evaluate the differences in style and seasoning that exist between different restaurants. Does this mean we don't enjoy food? That's ridiculous, we enjoy food so much that we enjoy comparing the immense variety of foods that exists in the world.
It's the same with headphones; each one renders the music (the dish by analogy) differently, and I find it fun to explore them and hear how my music will sound on each one. I find "gear vs music" to be an utterly false dichotomy. I wouldn't have gotten into so many different kinds of music if I hadn't been interested in headphones.
Sorry, longer OT ahead...
You do have a point here, and I think its not strictly "gear vs. music" but a spectrum. Still I think much is lost if one goes too far to the "gear" side of things since those two sides are not of the same sensory and emotional quality. To me the procedure at events is indicative: there's always the same music playing, and its reduced to pointing to differences in gear. I understand some (many) enjoy this, yet I'm not one of them.
I also like playing around with different gear, headphones especially, to see how some model works with my kind of music, maybe making it more fun to me. Which is also why I don't have fixed testing titles but use a more floating approach, listening to recent titles and judging rather fast if something is interesting to me or not. That makes recommendations a bit harder of course.
Due to age and experience I've also let go of the idea of "the one" long ago... I don't expect any single model to be the final holy grail, and I do enjoy the journey. I enjoy it so much actually that I mostly ignore the summit end of offerings (ok, I'm not that strict currently, having purchased the Composer, the E3 and considering the Stealth...) and dig through the midrange.
But I think there's one important point to make: I'm very much opposed to anything that has religious traits to it, i.e. fighting and dying for 1+1=3 kind of things. So this is my view on these matters, I respect any differences that are presented as arguments and might consider how they relate to my getting here (i.e. my point of view). I don't think there's any right and wrong here though -- after all its about joy, a deeply personal emotion. It's always interesting to discuss different views, and I think this is an important part of the hobby. Not necessarily the search for some truth, since we're all just seeing a projection of the actual thing. Going to cut off here, otherwise I'd have to copy part of Kants work into this post