Hi,
I've done the headphone thing. Reality is, after the $300~500 price mark, it's mostly novelty and veblen level purchasing for the idea of "summit-fi" rather than actual results that you can audibly appreciate. To even begin to appreciate flagship headphones, the source media has to be extremely high quality recordings. Not just high resolution, high sampling, big file size, lossless container, etc. The actual recording itself, the process it was recorded, where, how, etc. There' a few data bases out there to guide you on media to the better recorded albums. But this is the direction you have to go to truly even get anything out of a summit-fi level setup and even then, you'd be hard pressed to differentiate a $1k setup from a $4k setup with the same very high quality recording as a media playback to compare. At that point it's literally just personal preference. Just like in speakers. After $2~4k it just gets stupid expensive and there's no true quality gain, just other features you may care to spend on, but not an audible difference that is a true quality gain that you can appreciate.
I've done 40+ pairs, all the $300+ ones from the majors and all the $1k+ planars back when they really got popular. Now, everyone offers a "high end" headphone and a planar version or something. The market is flooded. I compared a bunch, did the A+B thing, changed sources, etc. And at the end of the day, the best most expensive headphones are not always the most pleasing to listen to. Just like speakers, some things may just sound better to you personally, and there's combinations for sure, such as matching an amplifier and headphone and enjoying the result, not just buying the best of the best and spending as much as you can just to end up realizing a $300 headphone on a $200 source setup sounds better to you than a $4k setup does, despite knowing the $4k setup costs more and should be better, but isn't necessarily.
Sometimes you have to just spend a bunch, get the top level stuff and then get that out of your system and feel fine knowing you've had the expensive stuff and you can finally let go of the placebo of it and just actually listen to the audio and appreciate things. This is when you'll find out that price does NOT reflect enjoyment when it comes to liking what you hear. You can spend a lot and get a neutral, sterile result that you just don't actually like to listen to your favorite music on. You can certainly get quality stuff and enjoy it. But like many things, there's too much psych-stuff involved, placebo and magical-voodoo-boolsheet that will cloud your mind and spray paint your ears with glossy gold paint. So my suggestion: buy a flagship mode, flagship amp and dac setup, go in a quiet room, use the highest quality recordings you can and evaluate it for a week and then return it (obviously buy from somewhere that allows returns). Get this out of your system so you can say you've had the $4k+ setup on your head and you don't have any higher order dream to look for. Then just enjoy listening. If you just get to a level of quality that is going to resolve 100% of the best recordings and stop there, this happens easily in that $500~$1k range with lots of room to spare, and just try a few and find something that you truly just like the sound of, it's natural frequency response, etc. Pro-tip: it probably will not be a truly neutral headphone! But find something you enjoy and then just STOP looking for more. Just listen! Enjoy what you have and spend a few years listening to it.
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So at the end of my 10+ year journey on high end headphone hi-fi, I actually ended up letting go of my most expensive setups and my favorite, all time favorite setup that was pleasing to me (the fit, the weight, the comfort, the overall sound signature, the natural frequency response, the resolution, sound stage presentation and how it paired with various sources) was actually a basic Hifiman HE-500 (the more efficient step from the previous HE-6 by Dr Fang) which I had professionally recabled with speaker taps and run it directly from a 50 watt speaker amplifier. I'm still listening to this setup to this day. 8+ years later. I have a massive thread on Head-Fi that is 240+ pages and many years old, we were all trying these inefficient planars on speaker amps. It got so popular that Emotiva re-released their A-100 amplifier to have a headphone jack with a jumper to allow it to output the full 50 watts of the amplifier for planars. But they key to my story is that.... just get a good setup that is reasonable that you just enjoy for how it feels and sounds, not something that you only like because it cost $2k~$4k. You'll get over that real fast when you spend $4k and realize a $1k setup sounded better to you. The result? You feel really wealthy knowing you could totally afford the better stuff, but your experience tells you that you enjoy something else and it's not about money it's about the enjoyment you get from what sounds good to you personally.
So my final setup, for over 8+ years now:
Hifiman HE-500 (professionally recabled by Brian at BTG Audio, speaker table cable, re-terminated posts on the headphone cups to be mini-XLR and balanced with a matching removeable cable that can be run balanced or unbalanced depending on which termination I connect to it with custom XLR 4 pin connectors with different terminations)
Maverick Audio TubeMagic D2+ tube DAC using the tube pre-amp output to an older Emotiva Mini-X A-100 speaker amp, running the headphone directly from the speaker amp's posts. It soaks up a lot of energy and sounds better, to me, than any other hifi setup I've bothered trying including all those big expensive Audeze stuff and all the higher end Schiit amps and stuff. I sold it all and kept my weird little Hifiman, Tube DAC and Emotiva speaker amp and it's been awesome and I still enjoy it. I don't even shop for headphone stuff anymore, for years!
Find what
you enjoy and just stick with it and enjoy new music rather than chasing some gear.
Very best,
