ICloud not syncing all purchased songs

I currently have three devices associated with my Apple ID: a Windows Vista desktop, a Windows 7 laptop, and an iPod 2 with iOS 5 on it. On each of these, iTunes is the most recent version. In each, I'm able to sync MOST of my purchased music from the iTunes store, but not all of it. I'm at just over a thousand tracks successfully synced, and 121 songs that won't sync. The music that I haven't been able to sync ranges from albums purcased at least a year ago to songs purchased within the past month. It's the same music that won't sync from device to device.
Essentially, the download previous purchases section of iTunes looks somewhat broken.
As can be seen here, I have "All Songs" selected, "Not In My Library" selected, iTunes is aware that there's 121 songs missing but isn't showing anything there. These are songs that I've previous purchased but which are not available for me to download. The window is identical on my laptop, and while the view differs slightly on my iPad due to the slightly different UI, a very similar thing is showing with exactly the same problem.
The songs still exist in iTunes itself as part of the same albums and with the same cover art; I seem to have the option of purchasing them again. So far, I haven't tried that. So, the issue definitely doesn't seem to that the songs are no longer available. I've tried to deauthorize and reauthorize each of my devices, I've restarted iTunes, the computers, the iPad, I've reset the iPad to factory settings and then tried again from scratch.
The end result is I currently have all my Flo Rida and Ke$ha songs, which sync just fine via the iCloud, but I'm missing Bob Dylan and Garbage.
Does anyone know if A) there's a solution, or B) Apple has acknowledged the issue and indicated that a fix is pending?

Posted this on another thread a few days back:
I have a theory about this. Could you all please check this? I have just sent the following email to my contact at Apple:
Hi Younus,
I may have noticed a pattern.
It would seem that the majority of the music which I am missing is that which costs £0.79. I have spotted in several albums where I bought songs that those which cost me £0.99 are still available from my purchase history to redownload, where those which cost me £0.79 are not.
I hope this will help you get to the bottom of the problem and would appreciate an update when the matter is rectified. In the meantime, I will continue to back up my music manually.
Examples of missing tracks:
"Disarray" and "Easier To Be" by Lifehouse. Purchase number: xxxxxxxxxxxx at £0.79 each are not available for me to redownload whereas "Broken" for which I paid £0.79 IS still available for me to redownload from my purchase history
"Broken Hearts, Torn Up Letters and the story of a Lonely Girl", " 4am Forever" and "A Town Called Hypocrisy" by lostprophets. Purchase Number: xxxxxxxxxxxxx at £0.79 each are not avaialble for me to redownload where as "Rooftops" which I paid £0.99 for IS still available for me to redownload for my purchase history
The album "Rocky Balboa: The Best of Rocky (Remastered) allows me to redownload every track (all at £0.99) with the sole exception of the first track "Gonna Fly Now (Theme From "Rocky" )which is THE ONLY track on the album costing £0.79. Purchase Number: xxxxxxxxxxxxxxx
I don't think is a co-incidence so would appreciate you feeding this back to Apple and seeing if this is a problem in other people's cases as well. If there has been a change in Apple's billing systems or something else this could be what has triggered this issue. This only started becoming an issue for me personally a few days after iOS5 was released so if anything changed at Apple's end around this time this could be to blame.
Could you please update me once you have fed this theory back to the business / engineers?
Thanks,
Mike.

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