Some songs won't copy to Ipod from Itunes

Hello all,
A bunch of songs won't transfer to my ipod and I can't figure out why...
Exact message: "Some of the items in the Itunes Library, including "..." were not copied to the iPod because they cannot be played on this iPod" Then it says there are "101 problems - see below"
I counted the tracks, there are actually 63. (My library has about 6000 tunes.)
I've recently upgraded to buy the new DRM free songs, but I don't see the connection.
I checked the Kind, Sample Rate, and Bit rate and there doesn't seem to be any differences between these and others.
I converted the songs to mp3-192s, trashed the originals, still won't transfer.
I still have 10GB of space left on my iPod, so it's not a space issue.
Most are songs I purchased in the I-tunes store.
The only thing these songs have in common is that they all were loaded in the same session.
They were on my iPod before I upgraded to 7.2
I'm on a G4 laptop, OS 10.4.9 1.67 PowerPC.
Running I-Tunes 7.2
Video iPod version 1.2.1

I was shocked to see your post. I was just about to paste this new thread:
After updating iPod software to 1.1.3 for my nano 8GB, there are 101 songs that iTunes refuses to sync to the nano, saying:
Some of the items in the iTunes library, including "Great Escape", were not copied to the iPod "My iPod" because they cannot be played on this iPod.
When I use the disclosure triangle to see details, all songs give the same info, for example:
"Multiply" was not copied because the file type is not supported by the iPod "My iPod".
But these are all just MP3 files. Some, if not all, of them were purchased in the iTunes store, then burned to a standard CD (aiff?), then later reloaded. They've all been played before on this iPod. I still have the original protected song files filed away, and I could pull them out, but I shouldn't have to do that. Has anyone seen this before? Thanks.
--Scott
Sully, I think it is an odd coincidence that we both have "101 problems". I thought this was an iPod problem at first, but I have reset the iPod and started all over. The problem persists. I think the problem is in iTunes. In my case at least, there seems to be a list of m4p files within iTunes that were on this iPod before, files that i have replaced with regular mp3 files now, and iTunes doesn't want to copy over them. Does anyone have any ideas? Thanks.
--Scott

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b noir:
your initial reply, which at first seemed promising, has now taken me to a whole other level of difficulty. allow me to elaborate.
1) i have attempted to play one of the aforementioned purchased songs in my itunes library, per your advice (not on my ipod, but on my imac). upon doing so, i get the error message:
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For the first time (I've had iTunes and an iPod for a long time), I'm getting an error message when I sync my iPod that says that "[s]ome of the items in the iTunes library...were not copied to [my iPod] because you are not authorized to play them on this computer."
Umm, what the f---? Why is this happening?
There are 103 songs that won't copy, and at first glance it appears that the first 103 songs I ever purchased are the very 103 that won't copy onto my iPod.
Anyone have any ideas about what is going on here? I am reasonably sure that I haven't copied all 103 of these songs to disc 5 times, or whatever the limit is.
Thanks in advance to all who answer.
TW

b noir:
your initial reply, which at first seemed promising, has now taken me to a whole other level of difficulty. allow me to elaborate.
1) i have attempted to play one of the aforementioned purchased songs in my itunes library, per your advice (not on my ipod, but on my imac). upon doing so, i get the error message:
"This computer is not authorized to play "______." Would you like to authorize it? The message box displays the Apple ID and asks me for the password.
2) all well and fine, except that the email address which displays in the message box as my Apple ID is old and obsolete--way obsolete. So of course, if I enter my present password, it will not match this old ID.
3) i attempted to change this old ID to my present ID. when I did so, my present ID, which DOES match my present password (and, thus, which i DON'T want to change), showed up as the ID to change.
4) what do i do? at this point i'm stuck.

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http://i1251.photobucket.com/albums/hh541/two250/itunesissue2_zps8ef2ead3.jpg
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Some songs won't copy to Ipod from Itunes

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