Can't transfer music from CD or hard drive to iPod.  Why?

I am having a problem adding music to my iPod that I ripped from a CD. Whether I open the CD with iTunes and try and add songs or use another application to rip songs, and then add through the hard drive, I keep getting an error message.
First, I try to convert to MP3 format (because I guess converting from the hard drive, the files are in WMA format). Then by reading the CD with iTunes, I try and drag songs into a playlist or into my library, and I get an error message that says "Error occurred while converting file name "Song_Title". An unknown error occurred (-223)."
I updated to the latest version of iTunes (March 06) and tried using the iPod updater and restarted my computer, but nothing worked. I didn't used to have this problem, but have noticed that the process of adding music has become progressively more difficult over the last year since I have had the iPod. I used to be able to get around it by ripping songs using another application and then adding the files from the hard drive, but that doesn't even work any more.
Help?!
Dell Inspiron   Windows XP  

You have to use iTunes. I believe there is a setting in the iTunes preferences to specify whether or not to copy media you import to the iTunes folder or leave it in place. Not in front of a copy of iTunes at the moment to check.  You MUST import it to your iTunes library, though, before you can sync it to the phone.

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