I actually wrote an article about WinAMP and where it's failing a little while back: http://s00techified.wordpress.com/2011/07/05/soo-what-happen...

WinAMP like so many projects ultimately needs a steroid shot. It was never supposed to be an iTunes. But it was supposed to be the go-to player for Windows Users. It's a shame it's just stifled. AOL should open source it.