How do I sync music from an external drive

Question

I recently moved all my iTunes content including music to an external hard drive (multiple reasons: space, SONOS capability, etc.). In addition, I purchased a new iMac. I can wipe the nano, no problem, but how do I get music from the external drive that is not on my computer (but which iTunes will play via iCloud) onto the nano?
Do I need to download everything back to my computer from iCloud and sync that way or is there some toggle I'm missing that allows me to load the external drive --> iTunes--> nano?
Thanks!

Answer 1

Jairy,
You may need to run through the following steps:
Once you've done that, follow the next set of steps to change your iTunes Media folder location to the new drive and then consolidate your library to the new location. This not only copies your audio and media files over, it also retains your ratings and playlists. Note: If you move your music and media to an external hard drive, you will need to have that drive connected to access your files. No matter what, it's always a good idea to have a backup of the media you have in iTunes.
Open iTunes.
From the iTunes menu, choose Preferences.
Click the Advanced button in the Preferences window.
Click the Change button in the iTunes Media folder location pane.
In the Change Media Folder Location window that appears, navigate to the location where you would like your new iTunes Media folder to be created.
Note: By default, your iTunes Media folder is a folder named "iTunes Media" in ~/Music/iTunes/ where the tilde "~" represents your home directory.
Click the New Folder button in the Change Media Folder Location window.
In the New Folder window that appears, enter the name of the new iTunes Media folder.
Click Create.
Click Choose in the Change Media Folder Location window.
Click OK in the Advanced window.
From the File menu, choose Library and then Organize Library if using iTunes 9 or later. If you're using iTunes 7 or iTunes 8 for Mac, choose File > Library and then Consolidate Library.
In the Organize Library (or Consolidate Library) window, select Consolidate files.
Click OK.  Important: This action copies all of your music and media files to the new location. There must be enough hard disk space available to copy all of your music and media files.
After the folder has been copied, locate your original iTunes Media folder, and drag it to the Trash. Important: Don't remove the iTunes Library files that may be in the same location as the iTunes Media folder. For more information about the iTunes Library files, see this article.
Quit iTunes and then open iTunes once more.
If you receive the alert "The folder containing "iTunes Library" cannot be found, and is required. Please choose or create a new iTunes library," you most likely moved the iTunes Library files. If this is the case, move them out of the Trash and back to where they were.
If you can open and close iTunes without encountering the above alert, empty the Trash.
iTunes for Mac: Moving your iTunes Media folder
http://support.apple.com/kb/HT1449
Cheers,
Allen