Try this, worked for me:

1) Launh ST:O without iTunes running.

2) Open the ST:O music player (making sure it is set to use iTunes inthe audio options).

3) press the "Play" button on the ST:O music player without going to iTunes first, it should start playing the first track in your iTunes library.

4) from here, you can switch to iTunes, start playing from a playlist instead etc. and it should work.

I think this is a result of the iTunes 11 update, it restructured the iTunes player and changed the library.db metadata file, they may not have changed the ST:O music player to compensate for this yet.

Anyone having this issue with iTunes 10.7 or lower?

Never used WinAmp, so I can't really comment on it, try the same workaround though.