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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Stax electrostatic headphones with the Stax power supply and amplifier.   I used them almost every day when the kids were small and went to bed early.  I have an older set, which in today's dollars would be roughly equivalent to the SR-L700 MK2.  If you can afford them, look no further!  They have held up amazingly well after all these years - ZERO failures or problems!
Thank you - I'm having some difficulty understanding what components are actually needed. Since I have essentially zero music source (CD, Vinyl, etc.) I'd likely just be buying music at a monthly cost, i.e. Tidal or qobuz I guess? Then I need to figure out whats the right way to get that material into a DAC->AMP->headphones? This is where I'm a bit confused, and hence my questions about what a "system" looks like. I.e. a fully functioning music listening experience on a table. 

Stax was one set I was looking at, and I'd like to try them out...
At your budget I’d shy away from a tube amp if you’re looking at planar ‘phones. While you can certainly build a very decent headphone rig for $2k, IMO if you can up it closer to $3k you’ll be at a significantly higher level of performance. Also, to keep costs down at least for now and if you have decent WiFi, I’d recommend running a USB cable from your phone or tablet (running Qobuz) to a DAC so it can handle the source/streaming functions until you can justify a better dedicated streamer. So, here is an idea for a pretty excellent headphone setup given what you’re looking for...

  • Hifiman Arya open-back planar headphones - $1599
  • Singxer SA-1 Class A headphone amp/ preamp - $599
  • Musician Pegasus R2R DAC - $1100
Just my initial stab at it FWIW, but there are other great alternatives to each of the above depending on your particular tastes. I think this system would synergize well and provide an expansive soundstage (for headphones anyway) with very good tonality and excellent and refined upper-level detail. Hope this helps, and best of luck building a satisfying system.
Thanks @soix for the thoughts and ideas. They're right on I think. 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...