Simple ? iTunes Question

Puerto - that's great, glad to be of assistance. I'm happy you have it under control. Thanks for the updates.

I'm not sure this solves your problem but you do need to specifiy the location of the iTunes music library if you want it stored somewhere other than the default, which would be the internal drive on you iMac.

Open iTunes and select 'Preferences' under the 'iTunes' menu at the far left of the menu bar on your iMac. Then click on the 'Advanced' icon at the far right in the Preferences dialog box.

The top box shows the current location of your music library, probably something like, "/Users/yourname/Music/iTunes/iTunes Music. If you want it elsewhere click the 'Change...' button and navigate to your external hard drive.

Here's more detail from the Apple support pages. http://support.apple.com/kb/HT1391

Puerto - It's hard to diagnose your issue from a distance but I suspect what you need to do is start over with the import process.

I tried to duplicate your situation by installing a fresh copy of OSX on a clean hard drive, which includes the iTunes application. I also attached another external hard drive to represent the one you want to have as your music repository.

I then booted up the computer from the external hard drive with nothing but the fresh operating system on it, opened iTunes and went through the process I described above to put the iTunes music library on the second hard drive.

I inserted a CD, dragged the music files on it into the open iTunes window on the boot hard drive, waited while they were copied and then checked their location. They were copied to the second hard drive, the one I had chosen via the iTunes preferences. Playing them from iTunes on the boot drive worked perfectly.

You may have already done all the work and no longer need this but there is an application designed to do automatically what you're doing manually. It's called Dupin' Lite. It's by Doug Adams, who has dozens of interesting tools for managing iTunes tasks.