Can't transfer music from iTunes

Hello -
Hoping for some help. I have a mini (1st gen) and after running iTunes and Ipod updates, I am no longer able to transfer music. When iPod is connected, iTunes recognizes that iPod is there and seems to allow me to drag and drop from the library onto the iPod (even tells me that the iPod is updating). But when I disconnect, there is no music on my iPod. I have tried the 5 R's and even deleted the iPod software from my computer, reloading the older version that used to work - to no avail. I now have a stylish doorstop - Help please!

I am having the same problem. NOTHING I do inside iTunes will add, delete, or change the music available in my iPod. I have tried everything.
iTunes appears to be updating my iPod, but changes aren't being made to my iPod. Very stupidly, when viewing the contents of the iPod via iTunes, it would appear that the iPod has in fact been updated with the latest songs, etc., but browsing the iPod itself reveals that this is not the case.
I am so frustrated. When I chose to "manually update songs and playlists", my iPod still would not receive the new songs that I dragged onto it, although it appears to be transferring.
As a test, I copied a song onto my iPod via iTunes, and then deleted the song from my hard drive. iTunes could not play it from my library (asked me to locate it), but iTunes could play it if I double-clicked it from the iPod's list of songs. I guess this is proof that the song is on my iPod somewhere but can't be accessed via the iPod itself.
Please help, I have tried everything and have been unable to listen to any new music for almost a month now. One time, after re-installing iTunes for the billionth time, my iPod finally updated itself to be in sync with what iTunes believed was on the iPod (that is, I could unplug my iPod and browse to the songs that I had downloaded to it), but after that, my iPod refused to reflect any new changes again.
Please help. I am so frustrated that I can't find any support anywhere unless I pay $$$ for apple's stupid support package.

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