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How much would I have to spend on headphones\IEMs to make this worth the difference?
I would say budget at least $300. After that, sky is the limit. Some very good options are available at $600, $1000 and $2000 price points. DACport makes them all come to life (we have a large collection in the office), but my personal favorite is the $300 Beyerdynamic 880.
Please no hate mail, guys -- I know that this is highly subjective :)