ITunes 11.1.5 will not sync to my iPhone 5

Hello,
My music will not update on my iPhone. It always looks like it is, but it isn't. For example, I added a playlist and I can't get it on my iPhone, but when I click the "on this iPhone" button it looks like it IS on my phone, but it isn't. I've tried the following (some more than once) and rebooted my phone after each attempt:
- Unchecking the box to sync all my music to wipe it all off, then re-checking the box and re-syncing it. That didn't work.
- Deleting all the music off my phone through the settings>usage menu. Re-syncing it to add music back. That didn't work.
- Dragging the playlist to the iPhone device. Again, it shows like it's there on iTunes but it's not.
The best part is that when I sync my phone, it keeps getting stuck on step 4 most of the time.
What am I missing?
Running OS X 10.8.5 on MacBook Air.

Purchase the Snow Leopard install DVD from Apple to install 10.6
After that uodate to 10.6.8 using Software Update

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