Short update today. Yesterday, I got iTunesDSM to correctly identify media files that were already present in the music folder and now keeps iTunes from creating duplicate files from those. I had to use the previous post's solution on how to read XML property list files to learn the location that iTunes stores music. The basic trick is to temporarily move the media file to an outside folder and then add the file to iTunes from that location. This is dependent on whether iTunes copies files to the media folder or not. There is still work to do as the number of options that are available are mounting. I have been debating on creating an Options object that just maintains all options the user would use. If I do then a new JPanel needs to be created that will list all the available options. I guess I got my work cut out for me.