I was able to convert the the wav to a 7.1 channel flac using audiomuxer, unfortunately I was still getting DirectSound buffer errors. I tried downmixing it to a 5.1 flac and it played just fine. I think this is a out_ds.dll limitation in winamp on any surround greater than 5.1 channels as it plays just fine in MPC/K-lite as you mentioned above.
Even tried it in wacup but still a no go
(┛◉Д◉)┛彡ʎɯouoıpɐɹ
Current status of Winamp: (Winamp 5.8) is not an ongoing project  get wacup
5.8 beta issue quick fix - Install 5.666 (there's no further 5.8 releases)
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