Itunes: can’t get playlist to play more than one song w/o having to manually hit “play”

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/

I figured out my problem:

I wasn't viewing a playlist, I was viewing a playlist folder, and it was showing me all the songs from each of the playlists in the folder simultaneously. When I clicked on the particular playlist, it let me remove the song from that playlist.

Makes sense! (I just wish they had put up a dialog box saying "cannot remove songs when viewing more than one playlist")