Tried and true recommendations: headphones, amp, source


So long story short - I’m trying to find my way back into hifi after a long bit of life experiences (see http://https//forum.audiogon.com/discussions/long-hiatus-from-audio-getting-back-into-it-speaker-room-help-please for context).

I think based on some thinking, I think I’d like to pursue a reasonably decent high(er) end headphone system for dedicated personal musical enjoyment.

My listening tastes are accoustical, strings, percussion, piano, vocals, jazz, some classical, and maybe a bit of light rock and roll.

Since I’m still learning exactly what I’d need, I’d appreciate folks sharing what they use in a dedicated headphone system. My preferences would be a tube amp, planar headphones, and a digital source/streaming (qobuz?) solution, and budget, lets say $2k? That’s flexible - but I’d like sort of mid-to-upper end gear in terms of accoustics and quality.

Thanks much, appreciate any guidance...
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My headphone recommendation is for Stax electrostatics. I have used them for many years and appreciate their clear, fast sound. As far as the price, there are many combinations of phones and amps to choose from. As an example, today on Audiogon I found a used pair of Stax 404 phones, with a tube amp (Stax, of course) for around $800. That leaves room in your budget for a transport and DAC. 
I use a Wyred 4 Sound DAC with the Fempto clock option.   It was a major step up from anything I have heard before, either in my system or at a dealer.   It is not the least expensive way to go but it is a good one.
I love the sound of my Woo Audio WA5LE with my Sennheiser HDV820 I also have the Focal Utopia, Hifiman HE1000-SE, Meze Empyrean & the Sony Z1R. All are very good, but for some reason I keep going for the HDV820s.
OP"I just bought a pair of HifiMan Sundara phones to try out, and since they're middle of the road I can start there and determine if they are "good enough" or if I want to try something upwards from there.
I'm also going to start building the DAC/Amp side of things and I think I'm starting to understand it"....
 First:head-fi.org...
 Second the Sundara are a SUPERB value & a true benchmark of neutrality under $1000.00!
 As for tube amps,with Planar Magnetic headphones stay AWAY from OTL amplifiers,they don't like low impedances.You want a Transformer Coupled tube amp for Planars..IMO a pure Class A solid state DAC/PreAmp/Head amp gets you everything a good tube amp does + better bass control & yes I've owned several tube amps but am now a Class A SS convert..Burson Audio makes some VERY organic sounding Class A gear & also Topping is doing some damn fine work as well...
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