I honestly don’t know what of my collection or previous headphones I would pick. I have made a hobby out of this the past 5-6 years and have found it even more complex than when I started. I have learned that comfort, sound and drivability aren’t everything. Longevity and quality of build are very important as well. Whether that’s availability of new parts at a reasonable price or the lack of noise introduction due to the build, it should be given as much weight as the standard main subjects. I have one headphone that sounds amazing but I can’t use because the ear cup’s click and crack for a good 20-30 minutes after putting them on, and given I have the bladder of a titmouse I’m taking them off every hour. Another one that I absolutely love, has proprietary part’s on it and the cost of a headband and pads plus shipping makes it so they’re essentially a one time use product with repair costing almost as much as the whole headphone, granted it’s not expensive to begin with but still. Throw in headphones that I have damaged due to an unfortunate yank onto a tile floor or stepped on because they fell off the bed…. there are a lot of really good headphones I have that I just have no desire to listen to. Oh one of them the adjustment mechanism doesn’t work anymore so it just slides freely. Another the jack went loose and it’s in pieces cause I can’t figure out how to wire the mini xlr I want to put on it.
With all of that considered there are three headphones that I use regularly and change between. Sennheiser HD6xx, Audio Technica ATH R70x Refine and Focal Elex. All three of them play nicely with tubes and the first two have great mid’s, with the Elex being more balanced sound and easily my most expensive pair of headphones. I’ve purchased 25-30 mid-fi headphones over the years and these three are the ones I wear the most.
If I had to pick just one chain of everything I’ve experienced it would be a good dac (smsl su9 or topping centaraus) a tube amp (darkvoice or dragon) and the Elex. (tube’s don’t play nicely with daily so I would add in a good solid state like a schiit magni or my topping A70pro)
But I do have a ZMF Atrium and Modhouse Tungsten being built right now so we’ll see how that changes.
Given that both of the last headphones cost more than every headphone combined on their own I don’t think that’s a fair comparison. I like to figure what I would do for a chain given a specific budget.
$50 budget, would be koss kph30 some grado pads and a dongle dac from apple. I could literally be told this is the only headphone I ever own and I wouldn’t complain, say you’d give me a million dollars but that’s the only headphone I can own (unlimited supply)
$150 Rode NTH-100 and any source; this headphone just tickles me right, I’m sure with EQ they become more balanced which I’ll have to try, but you could plug it into a potato and it’ll sound great.
$300-400 Moondrop Para1 and any source, they’re extremely easy to drive and something like an apple dongle dac would be fine. (maybe an xduoo mt-602 for a nice kick in budget)
$500 Sennheiser HD6xx and a little dot mkII with some left over for tubes. This headphone has been core to me knowing what I like in the hobby, I enjoy mid-high impedance headphones that enjoy tubes. I’ve focused most of my hobby around those factors lately. (mmmm maybe throw an extra $100 at a decent dac) I almost never recommend these though because I find it heresy to listen to them with onboard, they scale so well and just want tubes.
$900 Focal Elex (going off the price I saw them drop to not what I paid) and a darkvoice se336 with a solid $100 dac. These headphones give me the most joy out of all of them recently on my dragon.
Anything over that would be wasted money imo until you get into “hifi” which I’m waiting on my two pairs of headphones to arrive. These are due to me living through my midlife crisis and I’ve spent more the past year than I have the 5 years before that on a dac amp and two headphones.