SAFE Boot & Repair Permissions which should be done after any installations or updates of any software including the system on your computer.

Also, try disabling Classic ... then re-enabling it. It sounds like iTunes is opening it up right?

I wonder if a re-installation of Java might be in order. It looks like the action in LW is pointing to the wrong iTunes for some reason. I do know it is or was possible to change the audio program that opens up when audio files are completed.

Other things to try, Rebuild OS 9 Desktop, start Classic & rebuild desktop.

The problem may even be iTunes itself. The newer versions of iTunes have caused a number of people including myself problems.

* Oh another thing to try is deleting the LW prefs folder whilst LW is CLOSED; found here /Users/your_username/Library/Preferences/LimeWire