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Originally Posted by Formerly YB-2
That's a fairly large budget for something you've not tried. You can get an excellent intro with something like a pair of Sennheiser HD650 or HD600 or Grado 325 for well under $500 and a similarly priced headphone amp (either solid-state or tube). That will get you 80%+ of the way to the 'high-end' of $2-4K heaphones and amps.
As cleeds wisely states above, headphones are definitely not for everyone (as you can see, no headphone 'stuph' in my sig line) and you may find you are happy with some good ear-buds and something like a PDA (small, portable headphone amp/DAC with music in FLAC files on a micro-SD chip - will hold a few thousand CDs or connect thru various means to stream). Check the classifieds here. There was a nice Woo WA6 headphone amp available not long ago.
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Good advice.
The Senn HDs may not be the best bet as they are open-backed, maybe think about picking up a pair of Oppo PM-3's and a Schiit Asgard headphone amp with a true multibit DAC module in it for $399. My advice is to not dismiss Schiit gear because of the low price.
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Lumin P1 streamer/DAC/preamp, Constellation Inspiration integrated TT: Michell Gyro SE MkII, SME V, Koetsu Urushi Vermilion, EAR324. Harbeth 30.2s, REL R-305, Shunyata Alpha V2 ICs, Alpha V2 SPs, Sigma XC, Sigma NRv2, Omega QR-s & Alpha NRv2 PCs, segmented Altaira SG stack w/ Alpha & Omega CGCs, Everest 8000 PD. Remote Server Room: Uptone EtherREGEN, AfterDark Master Clock & LPS, Alita, Battle Angel, (Akasa NUC Roon Core), iFi DC Purifiers (for SMPS used for Alita & router), Shunyata Gemini combo power distributor & Altaira-type CG GP-NR hub, Venom & Alpha CGCs, Shunyata NRv14 power cords for digital components.
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