Can't put music onto ipod on itunes

Hello,
I'm a lifelong mac user, but I despise iTunes with an absolute passion. Here's the latest: I got an iPod (30gig) and want to select from among my 160 gigs or so of music and audiobooks (all mpegs) and put some on my iPod (onto the iPod icon, which does show up in iTunes). But when I put the files into my iTunes library and then try to drag them onto my iPod, nothing happens. If I try to move files from my music folder, the computer says they're moving, but then I can't find them on the iPod.
I have it set up to move stuff manually, not synch.
I have successfully moved playlists in the past, but I can't even do that anymore. The iPod itself seems to be working okay...?
Thanks for any help!

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

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I am trying to sync my entire iTunes library music onto iPod but iTunes 11 keeps crashing (using Windows 8 laptop)
I have tried to do it manually in little chunk and also tried the auto sync method too.
I have restored my ipod to factory setting 12 times now and retry but just when I think I'm getting somewhere iTunes freezes in the middle of the sync and then tell me it "cannot copy because of unknown error (-50)"
From then on my Ipod refuses to accept any more syncing, it may do one and then it freezes again, iTunes says there is an issue with iPod, so I run a scan fix, it is repaired but then iTunes wants me to "restore to factory settings" again, it's a never ending circle, I get it fixed, iTunes crashes and then I have to fix, restore and start all over again just to have the same thing happen all over again
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Hi, ktchinagirl.
Thank you for visiting Apple Support Communities.
There are a couple reason this issue could be happening. I have included a couple troubleshooting resources below that may help resolve this issue. Some of the articles are missing the steps for Windows 8, try the steps for Windows 7 as an alternative.
iTunes: May become unresponsive when connecting iPhone, iPad, or iPod touch
http://support.apple.com/kb/TS3219
Error 13, 14, 35 and 50 (or -50)
These errors are typically resolved by performing one or more of the steps listed below:
Perform USB isolation troubleshooting, including trying a different USB port directly on the computer. See the advanced steps below for USB troubleshooting.
Put a USB 2.0 hub between the device and the computer.
Try a different Dock Connector or Lightning Connector to USB cable.
Eliminate third-party security software conflicts.
There may be third-party software installed that modifies your default packet size in Windows by inserting one or more TcpWindowSize entries into your registry. An incorrectly set default packet size can cause this error. Contact the software manufacturer that installed the packet-size modification for assistance. Or, follow this article by Microsoft to reset the packet size back to the default for Windows:How to reset Internet Protocol (TCP/IP).
Connect your computer directly to your Internet source, bypassing any routers, hubs, or switches. You may need to restart your computer and modem to get online.
Try to restore from another known-good computer and network.
iTunes: Specific update-and-restore error messages and advanced troubleshooting
http://support.apple.com/kb/TS3694
This could be related to security software conflicts. If the steps above have not resolved the issue, I would recommend going through the troubleshooting steps in the article below.
iTunes: Troubleshooting security software issues
http://support.apple.com/kb/ts3125
Cheers,
Jason H.

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carlycarlycarly wrote:
Problem is that I can't drag music/audiobooks etc onto my ipod.
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