Cant put "purchased" songs on "iPOD"

Im sure its just because of this new version of iTunes I can remeber several updates where one was messed up and giving various errors. I think it was 6.2 to 6.5 and then a week later an update came out and fixed it.
I was using 7.0.2 and it was working fine. I recently purchased "korn unplugged" and "sevendust alpha" Now I can not manually move the songs to my iPOD.
I tried moving from one playlist to the other and that odly put the songs in the playlist on the iPod but the song count didnt go up and the songs didnt appear under IPOD>Music. When i click on the songs in the playlist i get an exclaimation point on the left like it cant find the file. Oddly enough the songs plays fine in iTunes, they just don't transfer to the iPod.
I deleted a song on the iPod, reset it and tested it, the song was not a newly purchased song and it went right on to the iPOD so i tried a "korn unplugged" song. Same thing happens, same results, cant transfer one of my newly downloaded songs.
Updated to 7.1.1 (which installed fine), but....same thing, old songs transfer fine new songs wouldnt transfer. My software for the iPOD is 2.3 and that is the latest version. I reloaded the software and that made no difference.
I know the 5 Rs and the hidden folder fixes, those didnt do anything.
I have never had a problem with my iPOD, but cant seem to quit having problems with iTunes and purchased music. All those filters to keep the RIAA happy are really messing stuff up, authorizing, protected aac's are annoying, they never used to be 'this annoying'
I have come to the conclusion this is another bad update for iTunes and next week there will be a fix. But if someone can persude me otherwise, im all ears.

Syncing to a "New" Computer or replacing a "crashed" Hard Drive: Apple Support Communities

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