Orang Utan
Maybe I like the misery
How's it done?
Cos I have 160 gig on my iPod and rather less on my Mac - my startup disc is full and I need to delete a load of stuffWhy would you want to do it anyway? Once you've deleted it from iTunes, it's rather more difficult to get it back from the iPod (not impossible, just requires jumping through a lot of hoops).
Just select the songs from your iTunes Music Library and drag them onto the iPod's icon in the bar on the left.
That's what I do all the time, anyhow.

Cos I have 160 gig on my iPod and rather less on my Mac - my startup disc is full and I need to delete a load of stuff
File - Library - Consolidate LibraryOK - another one, I've deleted files to make room for new ones, yet they still show up on iTunes with a ! next to them - how do I delete these so they don't annoy me whilst scrolling through iTunes
)I've heard the external hard drives can be unreliable.
I did this, but the CD that I added to the library is still there in my recently added folder - why oh why can't you just delete it from iTunes and it's gone permanently?File - Library - Consolidate Library
(note that this may move some music files around. this wil only annoy you if you have an anal file & folder system, which I doubt you do)

