Thanks for the quick reply!

So an expanded list of tasks could be:

1. Be able to play iTMS-bought music in iTunes on your computer (ie get it authorized)
2. Play an iTMS-bought song with iTunes
3. Play that song with VLC
4. VLC creates a key in C:\Documents and Settings\$USERNAME\Application Data\drms
5. Move your music to your new computer
6. Move the VLC-created key to your new computer and place it in C:\Documents and Settings\$USERNAME\Application Data\drms
7. Listen to your music on your new computer with VLC

Is this accurate?