I agree, but I think for anyone possibly reading this without the financial means to go whole hog on buying multiple flagships as I had, can also recognize that they can likely have an enormously satisfying journey without breaching the $1000 mark, and hopefully feel minimal FOMO.

There is so much capability and choice, while certain flagships might be someone's bag, I think it's important to acknowledge there is loads of high performing mid-fi available that may be more than enough to satisfy some people.

I really agree it's I'm important to start small, jumping on the wrong flagship could be a waste. i.e., I had the Beyerdynamic T1 flagship when it was brand new. I auditioned them with limited listening experience. I though they were good for a minute, then realized fairly quickly I absolutely hated them with large portions of my music library.

I tried out 16 pairs of Mid-fi, and some flagship level pairs. In the end my favourites were the modest Audio-Technica R70x, HD600, Grado SR-60 and Koss KPH30i. I sold the rest and feel great with what I have for the last 6 years ish.

For brand to brand comparison from my favourite pairs, I had the Sennheiser (HD650, HD800), Grado (SR125, PS500 and flagship) and Koss ESP-950 electrostatic flagship.

I'm not saying I disliked them these by any means at all, they were all quite impressive, especially for their time, but the ones over $1000 didn't necessarily connect with me any better... personally. So not even escalating by brand made the difference for me.

I tend to desire, dare I say prefer in my experience so far nothing more than Entry/Mid-fi tuned to my tastes. Where others may absolutely love certain pairs over $1000 they connect with. There may also be some I haven't heard, but would like.

My point is, exactly as you say, if I had had more understanding of my tastes back then, I may have avoided dropping big money on certain flagships that ultimately wouldn't connect with me, and could have better assessed headphones at any level more regarding my tastes.

Even then, I've heard much of the current increasingly megabuck level flagships, properly amped, my own music, time to listen, and just had no interest in the things I heard. Not one I've heard illicited the emotion and physical response I have listening to the R70x especially, or any of my other favourites.

The fact I can still jam out to my very first pair of Grado SR-60 and just get absolutely lost in the music, yet feel absolutely meh about bleeding edge $6000cdn headphone (before the cost of the amping them), probably speaks to just how personal the whole experience is.