deleting unchecked songs from itunes

Create a playlist to identify all the unchecked songs, highlight the whole selection that the playlist gathers up and delete them all at once. To identify the unchecked songs you'll need two playlists.

In iTunes go to File>New Smart Playlist

Uncheck "Match the following rule"

Check "Limit to", 25 GB (choose a value to suit the size of your library), Selected by Artist

Check Match only checked items

Check Live updating

To identify what's left (unchecked) , make a second playlist which will read the first one:

In iTunes go to File>New Smart Playlist

Match the following rule

Playlist>Is Not>Checked items playlist

Check Live updating

Once I have the Unchecked Playlist, I have to Edit the Smart Playlist settings to UNcheck Live Update, or Delete is not available for the tracks in the playlist.

But then, Delete only removes the songs from the playlist, not from iTunes, which is what I wanted to do. So how do you Delete (from iTunes) a grouping of tracks you only see in a Playlist?

When you say you want to delete the songs from iTunes, do you mean remove the files from your computer completely? If so, hold down control,shift, and delete at the same time (i think it's that way for windows). You will then be given the options to just remove the file(s) from iTunes only (yet keep the file(s) in your iTunes folder) or send it(them) to the trash, which will remove them from your music folder, and from your computer, (once you empty the trash).

To delete an item showning in a playlist from that playlist and from the library, hold Option (Mac), Ctrl (Windows) and press Delete.