Playlist does not contain new items after sync.

We recently pruchased 4 new songs from iTunes on the iPhone.
All 4 songs were successfully downloaded.  We Sync'd the iPhone with iTunes on a Windows PC.  All 4 songs are now in the library on the PC.
We then used iTunes on the PC to add the 4 new items to an existing playlist.  For what it is worth, we do all our playlist maintenance on the PC and then sync back onto the iPhone and our iPad because we find playlist maintentance on both mobile devices very clunky and time-consuming.
Once we added the 4 items to the playlist, we then sync'd the iPhone and the iPad with the PC again.  It all went smoothly as normal.  The new songs are in the 'songs' list on both the iPhone and the iPad.  However, the playlists do not contain all the songs on either devices.
The iPad sync options are set to sync the entire music library.  The iPhone sync options are set to only sync specific playlists - and I checked that the playlist that contained the new songs was selected for the iPhone.
I tried creating a new playlist on the PC with just the 4 new songs and sync'd it with the iPad - the new playlist appeared on the iPad, but it only had 1 of the 4 songs in it.
I added the same *new* playlist to the selected set of playlists to sync for the iPhone.  The playlist appeared on the iPhone, but this time with 3 of the 4 songs (one missing).  Random!  Worse, frustrating!
When I expand the device tree in iTunes on the PC (with the device still connected) to see what it thinks is in the playlist on the device, it always shows the correct content - but when you look on the actual device the content varies as above.
Can anyone shed some light on what has happened here, and preferrably, how I stop this random behavior and get this all back on track.
I believe all the software and all devices is up to date.  I am running iTunes 11.1.3.8 on Windows.
Thanks in advance for any help.

*** Update ***
We purchased another song on iTunes today.  We added it to one of our playlists on the PC and sync'd the iPad.  On this occasion the four songs we added to playlists yesterday all sync'd correctly.  However the new song we purchased today did not sync into the playlist.  I can't imagine why, but is there some kind of delay built into the sync'ing mechanism somewhere?

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