Syncing iPhone Misplaces Certain Songs in iTunes

I recently got a new SS external hard drive where I keep all of my music. I changed the iTunes (12.1.0.50) music library to correspond and it worked flawlessly on 600 gigs of songs. The weird part is whenever I sync my phone (iOS 8.2) to my computer (both wirelessly and lightning), iTunes misplaces around 100-150 songs that are also on the phone. Nothing changed in my phone, I can still play the music there, and the misplaced songs are still in the same directory as the rest of my library. I've manually found each song twice now (double-clicking each song with a next to it and searching in the library) and it's getting a little obnoxious. It seems to be the same songs each time my phone syncs, and a prompt always pops up saying that there was a syncing error and the music couldn't be located. Not sure there's a fix for it or what started the problem (switching hard drives, iPhone updates, iTunes update), but if there is I'd love to hear it. A quick fix would be to find a big batch finder to locate any missing songs in iTunes instead of finding each song one at a time but the ones I've found cost $. Thank you in advance!
Dan

Q: Are you saying that I could make a playlist and do something to it in itunes to make it compatible with iMovie/iDVD?
A: Exactly.
Here's what I am referring to per iDvd's Help Menu:
Click Here (twice)
Q: And to import an audio cd, will iMovie be able to import the files direct directly—bypassing itunes altogether?
A: You got it.
Click Here (twice)
(I don't think it's itunes causing the problem, or the protection,....
You may very well be correct. But isn't it at least worth trying to import directly from an audio CD as opposed to what you've been trying to above without much success? Give it a shot. What's the worse that can happen?
Message was edited by: SDMacuser

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Syncing iPhone Misplaces Certain Songs in iTunes

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