ITunes Lockup and Failed Sync

Recently, my iPod Classic 160GB somehow crashed when trying to sync a few new albums to it, and all my music was turned into "Other" and no songs appeared on the iPod. I restored the iPod but now there is a painstaking phenomenon:
I have about 15,000 songs, all of which are over 128kb/s bit rate. Clearly, that won't fit on my iPod, so I use the "Convert Higher Songs With Higher Bitrate to 128" option. The problem is this: Whenever I sync it, it takes a really long time, then eventually iTunes has an error window that says "2 Errors Occurred." When I check to see what they are, there are 2 "song not found" errors (which are always different songs) and another one that says "an unknown error occurred." When I close the box, iTunes locks up and won't sync till I format the iPod with Windows and restore it in iTunes. Only about 12 songs show up on the iPod at this point (even though it reached around 700 or more and the amount of audio data would suggest there's more than that).
I tried syncing about 300 songs without converting, and that worked fine, but then I tried to sync only 5000 songs with converting and it failed again. The worst part is that there is no error code or anything.
I'm trying to see if I can sync 1,000 songs at a time with converting and maybe that will let me keep them on the iPod, then I can add the rest in 1,000 song increments (which will take forever, but using Apple products is all about compromises!)
So, what is the deal? How do I fix this? Is it simply that I'm trying to convert too many songs at once (even though I did it before a few months ago)?

1) Open itunes, connect iphone, select what you want, sync.  To transfer purchases from iphone to computer: File>Transfer Purchases
2)Open itunes, connect ipod, select what you want, sync.
3)
iTunes: How to share music between different accounts on a single computer

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