iTunes purchased music won't transfer, everything else does

[pyarwood]

Please choose the appropriate forum for this topic. Thank you. I have version 4.1.7.30 of the iTunes software and have recently upgraded to version 2.3 of the iPod software.
It is a 3rd generation model.
My problem is fairly straightforward, I have 1648 songs in my library, but only 1604 of them will transfer over to my iPod.
This just started about two weeks ago after I upgraded iTunes to the version listed above.
That's when I noticed that none of the songs that are in my purchased music folder will transfer to the iPod, and the ones that used to be on there before I upgraded have been removed from the iPod but are still in my Library.
Any ideas on how to remedy this problem?
One other odd thing, there are about 13 songs from my purchased music folder that are on my iPod, but they are ones that I used to have stored on my 1st external hard drive, which crashed.
The remainder of my purchased music songs (the ones that won't synch) are stored on my current hard drive.

[pyarwood]

Oh, and I'm running Windows XP Home Edition.

[defaoite]

there are in your purchased folder but are they in your library, and can you play them in itunes.

[pyarwood]

Yes they are in my library and yes I can play them via iTunes.
I can't get them to my iPod though.

[defaoite]

this might be a stupid question but have you check that you ipod is set to auto sync. If it is have you tried rolling back the ipod update first to the previous version. Why did you upgrade in the first place?

[pyarwood]

I can't recall how to enable/disable auto-synch but I am fairly sure that it is still set up for auto-synch since it automatically adds new songs to my ipod after I have imported a CD to iTunes.
(And did so just last week)
I had to upgrade iTunes because I bought a song and they required you to upgrade to the new version of iTunes in order to complete the purchase.
I upgraded to the latest iPod software because I kept getting a reminder that the old version was out of date and iTunes couldn't update some of my songs.
In other words, I don't believe that the version of the iPod software is the problem, instead it seems to me that it's the latest version of iTunes that is causing the headache, but there doesn't seem to be a way to get around that.

[defaoite]

try burning the songs to cd ,and import them for the audio cd. This could be a digital rights issue. this should get around it.

[pyarwood]

Unfortunately I don't have a CD burner.
I did some browsing of the official apple support forums and it seems that a lot of people have encountered problems when they had to upgrade to the 4.7 version of iTunes.
However, my install worked ok, it's just getting a portion of the new version to work (purchased music synch) that's the problem.

[defaoite]

The only thing I can think of is to burn the tracks, If you have another PC, or a friend will let you borrow there's with a burner, you can authorize his pc to play your music, and then burn them from there ,as far as I know you authorize up to 5 pc's.