I don't know what your soundard DSP chip is, but I have a Hercules/Guillemot Game Theatre XP which features 20 bit playback.
Outwave.dll works for me in both normal and alternate settings for 24 bits, that is I am able to listen to Line Out. So I guess that in my case the 24 bits MAD sends are accepted by the soundcard, processed somehow and outputted. However, I cannot tell whether what I hear is 20 bits, or even the 24 bits downsampled to 16 (!!). So far, nobody I asked could find me a procedure without using an oscilloscope to find out what the real output is.
So I'm afraid that even if you manage to get sound out of winamp+MAD to the digital outputs, you won't have any means knowing whether this output is 16, 20 or 24 bits. Perhaps some experts can enlighten us ?
In any case I'd recommend mailing Peter Pawlowski - he should know whether his plugin is compatible to your card.
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