Maybe there are some problems of your iTunes. You need to uninstall your iTunes and then download the latest version from Apple official website. If it still doesn't work, you should use other third-party software like Leawo iTransfer to help you.
As a powerful iPod, iPad and iPhone transfer program, Leawo iTransfer provides perfect solutions for iPhone transfer, iPad transfer and iPod transfer issues. It's quite nice to transfer 12 kinds of files, like photos, music, videos, SMS, contacts, and so on between iOS devices, iTunes and PCs. It can also back up iPhone, iPad and iPod (touch) files to computer. Additionally, Leawo iTransfer is an outstanding music manager, which allows users to manage the playlists of the iOS devices and iTunes without limits. Moreover, Leawo iTransfer supports the latest iOS devices (iPhone, iPad, and iPod), iOS and iTunes.
You probably do not want to use iTunes for syncing your iPod music when you have got a lot of CD music long time ago, because iTunes can't sync them back to computer. "How can I transfer music to iPod without iTunes?" You may want to ask this question. Well, a powerful iTunes alternative is helpful on the iPod music syncing issue. How to Transfer Music to iPod without iTunes
For sync iPod music, i tried this without using iTunes:
How to transfer music from computer to iPod without iTunes
Hey! There are some other iPod Transfer tools which can transfer music between iPod and PC, iPod and iTunes freely. I am now using this Wondershare iPod Transfer which is very easy-to-use. Now I can transfer music between iPod and PC, iPod and iTunes easily. You can have a free try of it.
Hope that will be of help to you.
SOURCE: Syncing my itouch with itunes
Itunes can sync infinite ipods and should have no trouble, so there isnt a problem with having two ipods. Try this: turn off your ipod, hold the home button, and plug it into itunes while still holding the home button until a picture of the itunes symbol appears with a cable under it. itunes should say "ipod found in restore mode". this will get rid of any previous users' settings, and hopefully fix anything preventing itunes from syncing with your ipod.
SOURCE: I cannot sync my ipod touch
its possible that maybe some software has corrupted the touch, personally i have one thats jailbroken and when i sync it, none of my apps work, so my suggestion is to wipe it clean, and doing a shift restore
SOURCE: itunes library wont all sync onto ipod
first the easy part....1800 songs we will not move this one at a time..............plug ipod to pc..open itunes....see on left hand side of screen...pc (music,photo & video folders) and under that ipod (music, photo, video folders)..ok..click on pc (music folder) all your music shows up right ok..this time click & drag the pc (music) down to the ipod music folder and release....its 1800 songs so lets wait til the ipod is finish (look at the ipod file a circular motion is happening,,,,its loading).......once finish always eject your ipod...............now find where you are storing mp3 / mp4 on your pc...once you find it ..go to top bar view then click,on view details (artist,album,type,lenght) this where it will say mp3/4/wma/wav or flac file
SOURCE: i Tunes says syncing in progress but no music appears on ipod
Is the music tab checked under music?
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