Itunes: delete song from playlist

1. Export the source iTunes library as an XML file (File>Export Library…). This will create a file that holds information about the location, song filenames, and song rating!
2. Replace the file paths in your XML file with the path that the songs from the source library will be in when you import them. This path may point to your FireWire Drive, a DVD you have burned, or a temporary folder on your hard drive that you have copied your music to. Just to be sure of the new path, copy one of the files from this location to your library, export your destination library, and look at the file path to that song in the resulting XML file. To actually replace the file paths, I did a Find/Change in TextWrangler.
3. Set the preferences in iTunes in your source library to “Copy files to iTunes Music folder when adding to library.” This is under “Advanced.”
4. Import your library (File>Import).
5. Delete redundant files. If you’re like me, you have some duplicate songs in your multiple libraries. This is a tedious task, but I plan to do it over time.

http://www.kadavy.net/blog/posts/transfer-itunes-library/

ARGH -- never mind, I figured it out -- you have to have songs checked; it only plays the checked songs automatically, and skips the unchecked songs.

I wish iTunes handled some of these things a little more intuitively or at least gave you feedback if you're not doing things the way it likes.