What I like to see, are: Menu bar buttons to manage Winamp.
Here at my mac I've installed You Control Tunes
(see the big image below). Unfortunatly it works only with itunes. That's also the reason why I temporarily stay with itunes. It's handy, while I'm working. Instead of (continuously) switching to itunes, I can just manage it from the menu bar: Pause, play the former song again, or next song; Set rating stars, ectc, ectc. It's all possible. It's ingenious.
At windows I guess the app-bar at the bottom is good place.
It's nice to see also Vox Audio Player
makes use of menu bar buttons. And at Linux Ubuntu there is also menu bar button app (see the image at the bottom) allready integrated with the Ubuntu-OS.
Maby it's also possible, you contact the company who develop You Control Tunes, to develop together the Winamp integration? Oh yes, I would love that!
For now, I wish you lot's of succes. I'll keep watching for the Winamp development.
Kind regards from the Netherlands.