I remember listening to 5MMM on RealPlayer back in 1998 which was my first experience with streaming radio. Plenty of buff-uff-uff-ering but it still blew me away as a 12 year old.
As for my own story with MediaSpy, I first lurked in around 2007 or 2008, about the time DTV Forums radio section went quiet. I’m not sure if there was any radio discussion prior to this on MS (and radio is still very much a minor part of the current forum if we’re being honest).
I do miss dbrmuz from 2010-2013; I think he ruffled a fair few feathers but it was all good fun.