Existing iTunes songs won't transfer to my iPhone 5

Context:  iTunes 11.1.3 (8), iPhone 5 running iOS 7.0.4, Mac Mini running 10.9.1.
Some songs in my library purchased originally from iTunes won't transfer manually to my iPhone 5 manually.  I get an error message stating that the song's format is wrong.  These are songs that I've transferred to my iPhone(s) in the past without a problem. 
The problem seems to be related to clicking and dragging a number of songs simultaneously.  Occasionally, one or more of the batch won't transfer successfully and yields the error message about the format being wrong. 
If I click and drag each rejected song from my library to my iPhone, usually the song will transfer.  It may take one or two tries to make this happen successfully.
The rejected songs are in different formats (protected AAC, purchased AAC).  I haven't figured out a pattern for why some songs are not transferrable without special effort.
This is unique to the current version of iTunes and iOS 7.  I've never seen this happen before.
Any ideas for a fix/workaround?

What computer OS are you using? Do you have the latest version of iTunes (v11.1)? There has got to be a reason for the disconnect in the music syncing. I would recommend resetting the sync history. If you are in Windows, go to Edit, Preferences, Devices, and there is a button there. Now, with the phone connected to iTunes and the phone selected in the Device pane, you go to the Summary page and down towards the bottom of the page, there is a Reset Warnings box. After doing that, try to sync music again. If there is a problem, with the warnings reset, it should show up if there is one.

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