Hard question. Headphone is the most impactful of course but sound quality is subjective thing. It's not like buying a cpu for your PC. Stronger cpu is obvious. In headphones there is no such a thing.
I would spend below 1k for dac+amp and 3k for headphone. THX 789 $300, there is also top notch dacs around $400. Though simple magni/modi can be enough if you need a bit more headphone budget. Dac/amp market makes more sense when you fall in love with one specific headphone and wanna see it's performance with different dac and amp. Otherwise $100 magni modi baseline should work.
I must say the thread title made me pretty courious and I'm really quite surprised how far away most of the recommendations in this thread are compared to what I would do or recommend. I mostly agree with "chrisdrop", I think he got it quite to the point
Others though maybe not so much ... spending 1000$ on cables on a 4k bugdet or blow everything on an utopia is not exactly what I would do ^^.
For 4000$ you can get a used Stax 009 (2500$), a somewhat decent used Amp to drive it - there are not that many choices anyway so choose your poison (1500$), that leaves you 700$ for a DAC (for example a used Gumby), then you can still spend 100$ on a headphone stand, 50$ on a chinch or xlr cable - then you have 150$ left for your first months of your tidal or other high res streaming service
In the end it's all about personal preference at that stage but in my opinion and considering all factors that kind of setup is quite a bit ahead of anything that was mentioned here yet. If you want to go more mobile, a dap with a Abyss Diana or Diana Phi is hard to beat. I wouldn't overspend on the dap though. In the end these devices get old quickly and loose value faster than most audio gear.
The only way I can see myself dropping this kind of money on new gear would be speakers.
I can't think of any $4k headphone setup I would care enough for. My current IEM rig is about $1.4k and it's all I ever wanted. I'm now buying music instead of gear.
Spending the largest proportion of the budget on the headphones is tempting, but is by no means the only approach.
Eg, a dialed-in, multi-thousand tube amp can make a relatively inexpensive pair of headphones really sing.
Having said that, the Utopia driven by a high-end DAP might be the route I'd end up taking if I was under that budget and with no intention on upgrading any further.
Unfortunately, putting a concrete budget constraint as was posted doesn't really reduce the viable permutations as much as one might think. It still does come down to taste in the end, and still, the only way to be really sure is to live with a specific combination for dozens of hours' worth of listening.
Speakers is tempting but it is not that simple, room etc.. I would say nice quality sounding speaker system can be in the end very expensive, it definitely needs also good knowledge and trying, finding, good synergy.
Headphone It depends if electrostatic or planar/dynamic.
I want longer time try at home quality electrostatic headphone but when you search for quality electrostatic amp it is very expensive and not much options just SRM007 from Stax and than something from Mjolnir. But in this budget it is possible and the lowest money I would put is DAC.
If planar/dynamic I think it do not have to be that expensive and honestly not always fun to sit with it. I always liked idea off simplicity easy drive headphone via all in one system but there is not much headphone which is "really" easy drive. I think around $1500 is good sweet spot for headphone and than experiment with dac/amps.
And rest money I would put to the IEM it is fun with smartphone.
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