HDD to USB dac is vastly superior to using a sound card -- especially a PC sound card (even with Vista). Try a Wavelength USB dac (i have and love the cosecant) and you won't look back.
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I use a laptop and USB Turtlebeach Amigo to send toslink to an external PS Audio DAC III. Sounded good, but something wasn't quite right.
I changed to ASIO4ALL and added the asio plugin to winamp and it sounded much better.
Then, I stopped being lazy and plug in the USB cable straight to DAC. WOW! Things just keep getting better.
I have not had a chance to compare against CD as a transport but I have a feeling the PC will come close, but not better (I am using high bit-rate MP3 files). A future project will be using EAC to WAV to USB DAC and compare against a cheap CD transport.
If you stay PC (noticed, like me, that you ae thinking of making the switch to a Mac, assuming all is simpler and purer there) I'd give a listen to this:
1)EAC to FLAC (lossless open-code that has a Mac version too)
2)FLAC playback through Foobar 0.8.3 (older version, still sounds best), with the SSRC 24/96 upsampler plugin in Foobar
3) Out to your great PS Audio DAC III (USB doesn't like 24/96, so I'd try coax out w/resampling vs no resampling-with-USB; one choice will be better)
It's what I do (non-USB dac currently), but I'm gonna demo the Wavelength USB Dacs, and Gordon says I should go Mac. My own problem is when i ripped in FLAC I ripped to large album files and use CUE sheets (associated file that has all the tags, etc. and Mac doesn't support that mess). If I go MAc I'll use itunesencoder.exe and batch convert all to Apple Lossless and use iTunes on Mac.
Gotsouldr, if you plan to buy a new Mac, then it will come with the "Leopard" OS. If you have an older Mac or plan to buy an older, used Mac, then it may come with Tiger or Panther. Regardless, you should be able to run the latest iTunes with it. Mac OS older than Tiger will not support "Front Row" remote-control capability (there is a workaround).
Sound-wise, I do not believe there are differences between late model Mac OS'es.
Here is a link on a discussion we had about this:
Yes, I can hear the difference and it is significant with my DAC and system.
But given that all of this is subjective, I can't promise it will be better for you. Just the nature of this stuff.