I’ve gotten lots of interesting questions lately, many of which go deep into how iTunes manages files. The first one I look at asks about double entries for songs in iTunes. I also look at a possible way that Apple could add new, interesting smart playlist conditions, and I discuss holiday music, which you really don’t want to hear all year round.
Q: I moved some of my music files from the iTunes Media folder to an external hard drive. The tracks remained visible in iTunes, but unplayable (clicking on them prompted a dialog box asking to locate the tracks). I re-added the music files to my iTunes library, but now every track is listed twice. If I delete one of the listed tracks, the associated file gets deleted. How can I get rid of these double entries?
Read more here:: Ask the iTunes Guy: Issues with managing iTunes files