I would stay with iTunes on a Mac and convert the Flac files to ALAC with MAX. I say iTunes because I'm not sure if the other players get bit-perfect playback while iTunes definitely does.
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Headphones: HD600, SR225, D2000, SR60, PX100
Amps: CIAudio VHP-2, Minibox-e+
DAC: Zhaolu D2.5c
Sources: 16GB iPod Touch, 30GB 5th iPod Video, Macbook Pro, X-Meridian.
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