The problem with digital volume control is that not all algorithms properly address quantization errors
You need to apply dither in order to randomize quantization errors.
Chances are that the CD that you buy has had dither applied. Now if you modify the bits digitally and re-quantize it (at a new lower digital volume level) then you need to dither it before hand in order to avoid introducing non-random quantization errors.
iTunes applies dither in the recent versions - so you can be confident that the volume control is as good as analog. In older versions it was poor - it just threw away bits.
You need to apply dither in order to randomize quantization errors.
Chances are that the CD that you buy has had dither applied. Now if you modify the bits digitally and re-quantize it (at a new lower digital volume level) then you need to dither it before hand in order to avoid introducing non-random quantization errors.
iTunes applies dither in the recent versions - so you can be confident that the volume control is as good as analog. In older versions it was poor - it just threw away bits.