Itunes not finding songs

1. I very often get the message
"the song ___ could not be used because the original file cannot be found. Would you to locate it"
I have not moved any files but these happens recurringly.
2. itunes indicates that I have 27 GB of music but it syncs only 12 to the ipod. What happens here?
I have my files stored on an external hard drive which I sometimes have connected or not and to different USB ports.
Could this be the reason and if, how to solve it.
Any other programme available for free or to buy which resolves this better?

I would assume that it's because it's on an external hard drive. Because on windows xp, I found that this can happen really easily. The file location has to be EXACT. So...If you maybe moved a file, renamed something, or anything else, it freaks out and says that it cannot find the file.
I think that it is only syncing half probably because it cannot find those files you are talking about.
My advise to avoid this in the future is to change the setting in your iTunes and click on "organize my library". By doing this, whenever you import a song to you library, it automatically adds the file under the iTunes>Music folder under your "My Documents".
And also, try to see if you can find a setting where you can change the location of the iTunes folder that I'm talking about. (I'm not too sure how to do this, but I'm sure if you play around a little bit, you can figure this out.)

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