Cannot get iPod to sync with iTunes using Windows 8 Laptop!

Question

I have been trying to get my iPod classic to sync up with iTunes using my Windows 8 Laptop all night!  I tried restoring the iPod, I tried uninstalling/reinstalling iTunes, disconnecting my iPod to restart my laptop then plugging back in.  I also ran iTunes Diagnostics and it says my iPod isn't connected yet it shows on the sidebar.  I also have automatic sync set up.  When I hit sync, it initializes then stops.  What am I doing wrong?  Is there some trick I am missing.  Also, my iPod won't charge unless it is syncing.  What's up with that?
Any help or advice would really be appreciated! 
Thank you in advance.

Answer 1

For the charging issue, some newer computers with USB 3.0 ports (especially laptops) seem to have a "feature" that saves energy by turning off full power to the port when the connected storage device is no longer mounted by the system.  An iPod is a storage device.  When iTunes syncs the iPod, iTunes mounts the iPod's dlsk.  So it gets full power on the port, and the battery charges.  When iTunes is done syncing, iTunes automatically unmounts the iPod's disk.  The system shuts off full power to the port, and the battery no longer charges.
To work around this problem, go to the iPod's Summary screen in iTunes.  There is a setting their for Enable disk use.  Check that box and Apply.  This setting keeps the iPod's disk mounted continuously, when the iPod is connected.  Therefore, the port should continue to receive full power, and the battery charges.  That's fine for now, but later on, you can go into the computer's Control Panel preferences to see if there is a setting that disables this "energy saver" feature, and keeps the USB ports at full power all the time, whether the storage device is mounted or not.  If that is possible, you can turn OFF Enable disk use for the iPod.
NOTE:  WIth disk use enabled, you need to eject the iPod in iTunes before disconnecting it safely from USB.  The Eject button is next to the iPod's name in iTunes (to the right).
Now, for your main question about setting up automatic syncing...  First, if the iTunes sidebar (along left side of window) is hidden, from the menu bar, under View, select Show Sidebar.  When connected, the iPod appears in the sidebar, under DEVICES.
Select the iPod in the sidebar.  To the right, its Summary screen is shown.  Toward the top, there is a bar of buttons starting with Summary.  Click on Music there, next to Summary.  This Music screen is where you tell iTunes how to sync songs to the iPod.
Check the box for Sync Music.  This setting enables automatic syncing.  If you want your entire iTunes music library on your iPod (and it fits), choose the option to sync Entire music library.  Then click Apply.  Going forward, any change you make to your iTunes music library syncs to the iPod automatically (at the next opportunity).