IMO it's worth the extra to get the LCD2 Rev 2s. While I love the HE-500s, they fall behind in a majority of musical genres, particularly jazz and synth (my two favorites). I'll still pick them for classical, but most times I just plain miss the lush, natural mids and endless, effortless bass of the Audeze LCD2s.
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FWIW, Tyll also prefers the LCD2s to the HE-500s, even the Rev 1s.
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Yes, for me, the HE500s are preferable to all of these. They are simply musical and non-fatiguing, have great deep solid bass, have ambience, have more than decent detail, and are just plain natural and I
choose them often for my listening sessions and just don't want to take them off.
(Note: I especially like my Moon Audio Silver Dragon cable with them.)
I just yesterday found Tyll's Innerfidelity video review of the Hifiman phones and he seems to have come to the same conclusion that I have.
FWIW, Tyll also prefers the LCD2s to the HE-500s, even the Rev 1s.