Trying to sync music onto iPod but iTunes 11 keeps crashing

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
I have read here and there that there seems to be a bug in iTunes 11 when it comes to syncing.
I don't know what else to do, except revert back to iTunes 10 but I don't know how to do that either.
Anyone else had same issue syncing their library over to their iPod and how I fix it?

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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I have no idea what to do. I'm at a complete loss. I don't get it. I've tried nearly every fix that has been suggested online. I've tried all the different ways of syncing. I'm not syncing voice memos. I don't have any strangely titled tracks. I don't have any tracks that are unattributed to an artist or album. I have no duplicates. I have OCD, so my iTunes library, though vast, is kept in tip-top shape, and everything is ordered and tagged perfectly.
Wow. Hold the phone. I'm currently both overjoyed and even more flabbergasted. As I typed this long message, I left my device plugged into my computer. I didn't start a new sync- just left it plugged in. I happened to look at it just now, and, um, everything is synced. My iPod is working again. Still, this has become an ordeal that needs to be addressed. I'm scared to death of what will happen next time I want to sync new music to the device. I suspect more and more hours of resetting and fiddling with options. I want to stress enough that I'm positive this isn't a matter of me not being patient enough. Often times, I do indeed cut the sync short when no progress appears to be made, but I just as often leave it running for long periods of time.
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Again, using a 64GB fifth generation iPod touch updated to 8.1. 2GB non-retina MacBook Pro. OS X Yosemite. iTunes 12.0.1.26.
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Kind of a similar issue with me.
I've got an ipod touch that I use for my music only. The vast majority of what I have loaded in my iTunes library on my laptop is music I've imported into iTunes from my cd collection. I have several albums that came from non-iTunes digital purchases (cdbaby, amazon, etc), and then guess a few hundred albums purchased from the iTunes store.
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I'm not a 'technical' type of user so everything I was trying to correct the issue was pretty much just change settings options in iTunes on the laptop and/or settings on the iPod without any real knowledge or confidence that it would help.
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I completely set up the iPod again but used the option to not use iCloud (I don't use it to back up/store anything anyway). That attempt resulted in all my songs/albums syncing from the laptop to the iPod. Everything seemed to working fine for the past few months but then it happened again the other day. I had purchased a cd and imported it into my iTunes library... plugged in the iPod to sync everything and it wiped out all the non-iTunes purchased content again.
I deleted all the content off the iPod and did the 'out of the box' setup again and everything synced. Then this morning I purchased an album off of iTunes, hooked up the iPod to sync and again, it wiped out everything except my iTunes purchases.
This is getting beyond frustrating. The reason I've gone with apple all these years is because they are supposed to be 'idiot proof' for those of us that have a lot of knowledge of how/why all this works.

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