Why can't I sync my local files?

I just upgraded to ios8 and lost alot of my music. I deleted all the songs off the phone and tried to sync it again, but it only syncs the songs ive purchased through itunes, not the local files put on my itunes. How do i get the local files to my phone?

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Log in as an Admin User on your PC. Type 'Services' in the search area above when you click on start. (or see control panel and select Admistrative Tools.)
Select the Services shortcut. In the window that appears with your listed service, navigate to ipod service, Apple Mobile Device service, and, Bonjour Services. Doubleclick them to get the property page. Change startup to automatic, click apply. Then click start,
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Third party security programs, such as Kaspersky can also limit installations by User account installations, which adds to the problem. I have had a few installations fail, even in Admin mode - because Kaspersky sits on par with the Main Machine Administrator account for watching program and installation directories and registry keys - (which have higher privilege levels in some respects than the ordinary Admin account you normally start a new machine in before you add any other user accounts- all very confusing - but that's Microsoft all over for you.
Follow Ralph's advice if you do not have the necessary software already installed. You should install Apple's Application Management Software - which will look after the installation of all required elements for you and notify you of updates pending. In options have it set to Notify only - not all updates may be requred, and this option allows you to see what is being installed. It is good practice to set all updating software to Notify only - especially any thirdparty software - much of which carry all sorts of little 'extra's' you may not need or want.
It is also good practice to keep an eye on your Program and Features option in control panel, just to see what is being installed and when - including Windows updates.
Sorry about the long reply, but with December being your last sync - a lot can change in the meantime. Best be prepared.
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I'm having the same issue and the books I'm wanting to sync are checked. It worked on previous audiobooks that I had. In fact, I just finished the two that I had loaded and want to load two more. I only keep two books (4 files) on the device to conserve space. I'm using an iPhone 4 with iOS 4.3.3. there is 3GB free on the iPhone and I don't get any errors when syncing. My music is syncing fine and the books that unchecked were removed from my phone.
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[DISCLAIMER: My question is short, but my details are not. This is going to be a LONG read, but I wanted to make sure I provided all you helpful people with as much information as I could so that I could receive the best possible solution. So your patience and assistance is greatly appreciated!]
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a very disgruntled wizkid :\
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thanks for the tips thus far... everyone's so nice and helpful... I love it!
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Why can't I sync my local files?

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