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Personally I would suggest upgrading to new headphones, you'll see the biggest difference from that. If you can, try some out. Presumably you like open headphones, so i'll list a few highly regarded cans that would be a good step up. I'm not sure if all of these are within budget though, i'm used to UK prices. But if you can get a good deal and sell your old HD555s, it's probably doable.

 

Beyerdynamic Dt880

AKG K701/702

Audio Technica ATH-AD900

Grado SR325i

Sennheiser HD600

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Personally I would suggest upgrading to new headphones, you'll see the biggest difference from that. If you can, try some out. Presumably you like open headphones, so i'll list a few highly regarded cans that would be a good step up. I'm not sure if all of these are within budget though, i'm used to UK prices. But if you can get a good deal and sell your old HD555s, it's probably doable.

 

Beyerdynamic Dt880

AKG K701/702

Audio Technica ATH-AD900

Grado SR325i

Sennheiser HD600

While all solid suggestions, the DT880's are the ones that would work best with his soundcard, since his soundcard has such a high output impedance. 

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You're running a pretty good setup. The STX is a pretty good product overall and has very good value for money.  The next upgrade from that would reach around $400-700 for a DAC+Amp.

 

If you really wanted to upgrade your setup it would be better to upgrade your headphones as they'd give the most value for money. Source and Amp upgrades have really high diminishing returns

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You're running a pretty good setup. The STX is a pretty good product overall and has very good value for money.  The next upgrade from that would reach around $400-700 for a DAC+Amp.

 

If you really wanted to upgrade your setup it would be better to upgrade your headphones as they'd give the most value for money. Source and Amp upgrades have really high diminishing returns

Hmmmmm.

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