Which Headphones? Headphone System or buying components?

I started listing to higher quality songs recently, flac, up to 24 bit 96kHz, but they are playing through my Thinkpad Laptop and Bose Tri-Port Headphone. After reading through lots of blogs and Stereophile.com I decided to spend some money on a better listening system. My spending limit is $2000, thank you Tax Refund. Anyhow, I though about buying better headphones, either AKG 701, Sennheiser 650 or 600, and of course a DAC/Amp, I was looking at the Benchmark DAC1 Pre or USB. So I have few choices and don't know how to decided on which headphones to buy and which DAC to buy.

The Recording Angel

The Recording Angel

Back in the last century, I mused in this space about the essential difference between recorded sound and the real thing. I had been walking to dinner with friends when I heard the unmistakable sound of live music coming from a window. But here was the kicker: rather than the instruments being of the audiophile-approved acoustic variety, they were two amplified electric guitars. Their sounds were being reproduced by loudspeakers, yet it was unambiguously obvious that it was not a recording being played through those loudspeakers, but real instruments.
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