Haven't heard your setup, but I love my ipod classic 160 and wadia transport feeding a benchmark dac 1 and Threshold gear. The sound is fantastic.
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I'm using a 170i + Benchmark DAC. The sound is great and I like the convenience of putting together playlists and easy access to my collection. For most recordings I find it indistinguishable from the CD's played on a Marantz SA-11S1.
imho the sound quality from the Benchmark DAC was much improved when using a preamp - Bryston BP-26 versus running straight to the power amps - 7BSST's.