Ok, I'm gonna give you an alternative to iTunes.
1. Download RealPlayer (free download) here:
http://www.real.com/ (Don't get the Super Pass version, just get the basic Free one)
2. Run the exe and install it
3. Fill out any forms Real Player gives you, and then launch the program.
4. Underneath the Play/Stop/Pause buttons and that, there will be tabs, they are Real Guide, Music and Library, Burn/Transfer, and Search. Hit the Burn/Transfer Tab.
5. Once you're in Burn/Transfer, up at the top theres a bar with File, Edit, View, etc., in that bar hit the Tools button and then the Add a New Device button
6. It will open a new Window. At the moment, the Featured Music Store Device is iPod, but that might change in the future. If it isn't when you're looking at it, on the Find a Device box in the bottom left corner, select the drop down menu next to Browse and hit Apple. To the bottom right a box with an Ipod picture in it will come up. Three links will be beneath the picture (these three links will be under the picture if its Featured Music Store Device as well) the links are:
1. Get Firmware | 2. Install Device
More Info
7. I'm assuming your iPod is up to date. If it isn't you can update with the Get Firmware link, but if it is, hit 2. Install Device
8. Real Player will install the device, then restart
9. After its restarted, head to the Burn/Transfer tab again
10. At the top below the tab Burn/Transfer there will be something that says Current Burner/Device:
11.Insert your iPod if you already haven't, then select it in the Current Burner/Device dropdown menu.
12. You'll have the library (the left hand side box), where you can drag your media files, then after they're in your library, click and drag them into the right hand side box, the iPod.
13. But before you do that, go to options and click reset iPod and everything will reset causing it to be fixed. Everytime you update your ipod click on eject device (you'll understand once you do these instructions) and it will work fine.
