I would look for a Focal headphone in you price range and look to Schiit for a DAC. Focal are really efficient and well balanced and Schiit is great budget gear. I have several pieces of both. You can see my primary headphone system under my user ID.
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Sennheiser tend to be a bit more trebly and less full bass unless you can provide enormous power to them. I swap my Focal Utopia and Sennheiser HD800s all the time. I used to listen to my Focal much more than my Sennheiser until I got my big Woo 300B amp (~$7K)… finally the Sennheiser have perfect tonal balance and airy er… but the Focal still have better bass.
@ghdprentice Since you mentioned the HD800’s I’ll jump in and tell you about how I run mine.
I got a custom wired Cardas clear to a pair of XLR females so I can plug them directly into my Atma-sphere pre amp since Ralph stated it can drive headphones well. I’ve never had a dedicated headphone amp to compare, but I’m pretty happy with the results. I have done the felt/foam ring mod, and have removed the dust covers, all to good effect.
With your budget, I'd give the Massdrop x Sennheiser HD 6XX a look. I have about a dozen headphones including a few costing 10 times as much or more and they are the ones I reach for the most. They aren't "audiophile" headphones, in the sense that there are others that have more detail or punchier bass, or are better in other ways, but they are really easy to listen to, just a tad on the "warm" side, and super comfortable and relatively easy to drive. They are basically a rebranded HD 650 which retail for around $500-$600 if memory serves me correctly.
That leaves you with enough money for a decent DAC. A Schiit Bifrost and the HD 6XX should leave you with some money in your pocket and provide lots of enjoyment.
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