Cannot sync playlist to iphone 4

Hello there
I have iTunes 10.6.1.7 installed on my Windows PC which is running Windows 7.
I have iOS5.1.1 installed on my iPhone 4. I still have 7GB+ free on my iPhone.
For the past few weeks I have had problems syncing a playlist from iTunes to my iPhone.
The playlist contains 68 songs but only 2 songs sync. About a third of the songs have been purchased on iTunes, the rest are burned from CD.The individual songs are in my music library on my iPhone and play individually with no problems.
This is a new playlist. When I first started having this problem I deleted my old playlists from both my iPhone and iTunes, synced my phone, disconnected it, and made a new playlist. When I synced, the same 2 songs were the only ones to sync.
I have the Sync Entire music library selected on my Sync Preferences.
I should add that I am based in Ireland, do not use iTunes Match (it's off on iTunes and iPhone) and do not have music backed up to iCloud.
This is extremely annoying. Any help would be appreciated.
Thanks.

Hello Smithfiledhokie,
Thank you for contacting Apple Support Communities.
Is the cloud you are seeing on your phone one of these icons?
Cloud with an arrow pointing down
The song is stored in iCloud and available to be downloaded to your computer.
Cloud with a diagonal slash
The song isn’t eligible to be uploaded to your iCloud library. For example, the song file might be larger than 200 MB, or encoded at 96 Kbps or less.
Two clouds with a diagonal slash
Your iTunes library contains duplicate versions of this song, and only the other version was uploaded to your iCloud library.
Cloud with dotted outline
The song is being matched, but the process hasn’t been completed yet.
This is from the following articles:
iTunes 11 for Windows: Symbols used in iTunes
http://support.apple.com/kb/PH12306
iTunes 11 for Mac: Symbols used in iTunes
http://support.apple.com/kb/PH12106
The following article will explain how to download previous purchases:
Download past purchases
http://support.apple.com/kb/HT2519
Regards,
Jeff D.

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