Certain songs won't go to my iPhone 4

- Everyone in my family uses a different Apple ID
- I recently took lots of songs from various family members iTunes and put them in mine via Home Sharing
- I updated my iPhone 4 to the iOS 7 beta with a complete restore
- I then switched it back to iOS 6.1.3 via a complete restore
- Now, all songs from my mother's iTunes won't go to my iPhone 4
- I have tried de-authorizing and re-authorizing the account, un-checking and re-checking the songs, and everything else, but they still won't go onto my iPhone 4
- All software is up-to-date

Anyone know how to fix this???

 

They're all songs that were bought on one Apple ID from the iTunes Store and transferred to my laptop (which is authorized to use 5 Apple IDs, including the one that bought the songs). I've never had this problem before, and it is only happening with songs from this account. The songs play in iTunes on my laptop, they just won't transfer to my iPhone.

 

Anyone have an idea of how to fix this?