Why do my songs and audio books keep getting erased when I add a new book? Now some books will not play and the iPod does not keep track of where I was when I pause a book, leave for music and then go back!

About a month ago I added some new audio books to my iPod Classic and then after disconnecting, I discovered EVERYTHING had been erased.
I had to restore through my iTunes but then I could not load my music back on.
I uninstalled / reinstalled iTunes and completely reformated the iPod drive.
I successfully got my music and books back on but then added a new book two days ago only to discover everything got erased AGAIN!!!
Of course, my 1 Year Warranty was up about a week before the first incident.....
I formatted the iPod again, uninstalled / reinstalled iTunes (it was freezing during sync) and downloaded all my music and books again.
Now I have several books that will not play (they play on iTunes and they played on the iPod before all these events) and the iPod does not keep track of where I was in a book when I have to stop and go to something else.
Does anyone know what is going on with this thing??? I have a 5th Gen Video and in all the years I've had it, I've NEVER had problems like this!
Does anyone have any ideas on what I can do to get my iPod Classic up and running properly again?
Thanks.

When iTunes/iPod sync process failed due to timeout, the iPod, has only the initilaised filesytem structure at the start of the Sync.
The timeout failure could be due to
Bad hardisk - do the iPod disk diagnostic, refer to this excellent post by tt2
Slow USB port or resource - Dont use any USB hub, disconnect all other USB devices while syncing
Timeout due to Antivirus or other plugins - disconnect from Internet and stop the Antivirus or monitoribng software if you are syncing.
Preferably stop doing other things while syncing this ancient device, which the latest iTunes designer, think will soon be extinct.
Have a nice day!

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