ITunes failing to send songs to iPod

I have had my iPod for over a year now and have had little difficulty interacting with the iTunes software until recently. After downloading the new iTunes update, all of my music on my iPod was cleared for reasons unknown to me. I updated the software on my iPod and have the latest version of iTunes. Now when I connect my iPod to the computer and iTunes tries to transfer my library of about 1000 songs to the iPod, there appears to be some error when it gets around 200 songs in. It says Updating Ipod at the top of the screen, but it will get stuck up on a different song. It will do this for several minutes and then freeze up. I close out iTunes and disconnect my iPod and no songs have been transferred. I don't understand why it would work perfectly for over a year and suddenly have these problems. I can't get the songs to transfer to the iPod and haven't been able to get past about 400 songs max before it freezes up. Please help, I would greatly appreciate it.

Okay, I did what I was dreading and completely restored my ipod using the updater, then I uninstalled and reinstalled itunes. Now, it will not allow me to update my ipod with the music.
edit: specifically the "Update Ipod" option is greyed out.

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you know, i had this same problem - EXCEPT that it's
my own computers!! i had an itunes library on one
computer (that were ALL SONGS that i either bought on
itunes or transferred from my BOUGHT cd's. i then
recently bought an iMac, and am trying to transfer
the music to the new computer, but it will not let me
do it in iTunes since it says i cannot sync with more
than one iTunes without erasing the iPod. any
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http://docs.info.apple.com/article.html?artnum=300173
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I have a real nice Acer ultrabook with windows 8.1 64 bit, it runs really good with pretty much everything, no problems whatsoever.
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YamiPod Mac and Windows Versions
iGadget Windows Only
iPod Access Mac and Windows Versions
Music Rescue Mac & Windows
iPodCopy Mac and Windows Versions
TuneJack Windows Only
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Provided the files were properly tagged then iTunes should pick up the data when the files are imported into the library. The main problem is usually any files in .wav format.
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Itunes not syncing all songs from ipod.

I just got a new laptop...downloaded itunes.....and plugged my ipod in. iTunes only took a few of the songs from the ipod? (55 out of 499) Why? Have no idea how to fix this

- Unsync/delete all music and resync
To delete all music go to Settings>General>Usage>Storage>Music>Tap edit in upper right and then tap the minus sign by All Music
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:
iOS: Back up and restore your iOS device with iCloud or iTunes
- Restore to factory settings/new iOS device.

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So recently my computer crashed and my hard drive had to be replaced. I got my computer back a couple of days ago, only all the programs and files had been deleted. All of my songs are on my iPod, but I just downloaded iTunes again and it is completely empty. I'm not sure how to connect my iPod to my computer and have it put the songs back on to my computer without clearing the memory on my iPod. Does anyone know how to do this?
Thanks.

Open iTunes and select edit/preferences/advanced/general. Put a check mark in the box marked "copy files to iTunes music folder when adding to library" and also "keep iTunes music folder organized", then click 'ok'.
Connect the iPod whilst holding down the shift/ctrl keys to prevent any auto sync, and if you see the dialogue window asking if you want to sync to this itunes library, click 'no'.
Then go to file/add folder, open 'my computer', select your iPod and click 'ok'.
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If this doesn't work (and it may not because officially it's not supposed to), there's Yamipod. This is a free program that transfers music and playlists etc from iPod back to the computer. However, it does not transfer playcounts/ratings etc.

ITunes failing to send songs to iPod

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