How do i use an external hard drive in conjunction with my itunes account?

I'm having so much trouble locating music from my itunes account that i previously transferred onto an external hard drive.  I regularly get messages with each sync i try to do telling me that songs could not be located.  Also when i try to play certain songs they have a circled in front of them which prevents me from playing them even on my computer.  I've tried everything in my knowledge to rectify this problem but i just cannot find a solution. Please help.

Hello ryanbenson,
With this issue its best to start from scrach.
-Create a folder on your external, call it itunes music.
-Find all of your music on your computer and cut and paste it all into that folder.
-In itunes click music under library on the left and delete all of your music.
From here you want to add everything back into itunes from the itunes music folder on your external.
-At the top of itunes click edit, prefrences, then advanced.
-Make sure keep itunes folder organized is checked.
-Make sure copy files when adding to library is un checked.
-At the top it shows iTunes media folder location, to the right of that you can change the location to the external hard drive, to the itunes music folder.  You will have to keep the external connected to play songs in itunes and sync but this is how my itunes is set up.
-Click ok on the bottom right of the prefrences window
After all that,
-Click file at the top, then add FOLDER to library
-Navigate to your external and click the folder that has all the music.
-Click ok or add folder or choose folder
From here all music will start importing back into the library. iTunes will stay organized. You will be able to sync and play your music again.
Hope this helps.
~Julian

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