Is there a way to delete from iTunes Library & Computer?

I am trying to clear out my iTunes library with songs I dont want anymore. I want to go through the library and delete the songs, but I also want them deleted from the computer so that they dont get back into my library later. I know that my iTunes used to give me this as an option when I deleted a song in the library, it would ask me if I wanted the song deleted off my computer too. Now it doesn't ask me anything, it just deletes it off the library and not off the computer.

Additionally, I would also like to do something else but I'm not sure if its possible. Ultimately I would like to be able to make a playlist (an on-the-go playlist) of all the songs that I no longer want. This way I can just go through my ipod and select the ones I dont want when I have the time. Then I would want to delete all the songs in the playlist off my iTunes Library as well as my computer. This way I dont have to go through and delete each song indivually. Thanks in advance for your help.

Also, is anyone else having trouble with CoverFlow? I'm getting a touch for Christmas so I'm trying to get my album art sorted so I can use CoverFlow, but it keeps making seperate albums for songs on the same album. Googled it and some other people are having this problem too but I didnt find a solution.

According to the itunes help file, it only asks you if you want to permanently delete if the file is stored in the itunes music folder (My Documents/My Music/iTunes). Otherwise you have to locate the file and delete it manually.

I don't think you can permanently delete from on-the-go regardless of where the file is stored. That's all I have.

Alright thanks. I did find out you can delete from a playlist and iTunes library at the same time if you do Shift+Delete but that wont help me if it doesnt delete off of my computer too. My files arent in the iTunes music folder they are in a seperate one so I guess I'll have to manually delete.