Problem using external drive as library for iTunes

I am using iTunes on a Mac, with a linked hard drive as the library for my music. Using the "add to library" feature, I am able to link the music on the external drive to iTunes (given the size of the library, I don't want it added to the Mac hard drive). This works perfectly until I need to reboot the Mac. After rebooting, all the songs in iTunes are displayed with an exclamation point and iTunes needs to be individually directed to their location. Basically, I am forced to add the entire library (and remove all the old songs) every time I reboot the Mac.
Is there a better solution to this? In addition to being inconvenient, it also causes me to lose all my old playlists, so I would like a more efficient solution to keeping the library after rebooting.

It sounds like the locations of your music files is not the same as the location identified within iTunes. In Preferences / Advanced, make sure "Keep iTunes music folder organized" is checked and verify that the location of your iTunes music folder is the same folder where your music files are located. If it isn't, you are going to want to change the location to the folder on your external HD and then consolidate your library. The next time you start iTunes, you won't have to re-add your music to your library as iTunes will be able to find it.
Click this link for clear direction on the necessary steps.

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