After purchasing a DAC with a wide range of supported bitrates,
I searched for a ASPI plugin for Winamp and came across this one:
https://sourceforge.net/projects/out-yasapi/
Tried it out and it works perfectly!
I suggest the complete package download with GTK libraries.
Real plug and play installation.
Shoutout to PBelkner if he still roams these forums.
Cheers!