ITunes will not allow me to put songs on my Ipod...

I updated my itunes and ipod and everything. I've had my ipod for a year now and have never had a problem like this. I drag my songs from my music folder onto my ipod itunes area and it says it's putting it on my ipod but when it finishes the song(s) are nowhere to be found. I have like 2500 songs on my ipod and numerous videos so it's not like I've never done this before. It only happened when I updated to the new iTunes so I figured I'd uninstall it and put back the old itunes I had which was iTunes6.0.5 and I get this error now when I try and open it:
[IMG]http://i47.photobucket.com/albums/f161/puhpuhplaya2/itunes.jpg[/IMG]
Can anyone either please tell me how to fix that error or tell me how to fix the problem with the new iTunes because I'll re-install it if someone can help. Thanks.

I installed itunes 06 and now it will not allow me to put my purchased songs on my ipod. I get the notice that my computer is not authorized. Yet, each time I try to authorize it, I receive the notice that authorization was successful and there is only one computer authorized. I never had this problem before I installed itunes '06. Can anyone help? It sounds like the same problem the person before me had.
imac   Mac OS X (10.4.8)  

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