So have you narrowed your problem down to tagging with winamp? To one of the instances where it doesn't use freeform text?
All my self-ripped music has been tagged with AudioGrabber - it all shows up properly in emplode, Winamp and Tag Studio. A bunch of other files I've stripped and tagged with Tag Studio. They also come up fine in emplode and Winamp.
My current genre beef with emplode is "AlternRock" instead of "Alternative Rock" - and the fact that it doesn't store new items you manually input.
Bruno