Depends on the DAC and the CD player. Lets assume that the FLAC file was ripped from the CD you'd be comparing it too, making the data essentially the same; it would come down to the DAC in the CD player vs the USB DAC you're using. The superior DAC would give you a superior result.
FLAC on the laptop line-out would be the worse
It would be more cost effective (for a given audio quality) to add a USB DAC to the laptop, then to buy a "high end" CD player.
Depends on the DAC and the CD player. Lets assume that the FLAC file was ripped from the CD you'd be comparing it too, making the data essentially the same; it would come down to the DAC in the CD player vs the USB DAC you're using. The superior DAC would give you a superior result.
So the reason people pay thousands of dollars for a high-end CD player is partially for the integrated DAC inside? Would you say that nowadays, most high-end audiophiles have switched over to listening to FLACs via a laptop instead of CD players?
It depends I suppose. From either a CD or from a file on your computer, at some point a digital to analog conversion has to take place. In the case of a CD player, that can happen in the player and you can run analog outs, or you can run a digital out to a preamp (in the case of a traditional stereo) and use the DAC in the pre amp. At least that is it in a the simplest sense.
There is more to it though... I don't believe you could take a cheap CD player, run the digital coax out to a high end preamp with a good DAC and the get same results as you would with an expensive CD player.
I think most audiophiles still use CD/SACD's fro their source, but I could be wrong. In my experience, getting high quality files is hard and inconsistent. Discs or vinyl are still the way to go (I find).
I would imagine that new DAC's out preform more expensive DAC's from the past. That's the way technology goes.
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