Cannot delete songs from iPod when in manual update mode

Hi
I am using iTunes 7 and i'm trying to delete some songs just from my iPod and i have always used the manual update option.
The problem is when i go into the songs on my iPod and go into a playlist and try to delete the songs within a playlist it won't let me. BUT when i search for those same songs within my iPod library (library shows all songs on the iPod) i can delete them.
So my problem is i cannot delete songs within playlists just from my iPod. I know that deleting the playlist on the left hand side navigation bar will still keep the songs there, it will only delete the actual playlist.
Also when i select a song(s) the edit menu is all greyed out except for copy.
Can anyone help please.
iPod 5th Generation + iTunes 7 Windows XP Pro
Windows XP Pro
  Windows XP Pro  

Try using the key combination Shift-Delete when deleting from a song from a playlist, this will delete it from the library as well.

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