IPod resynchs when A LOT of unchanged songs, does not pick up new playlists

Question

My 60 GB iPod classic crashed big time, requiring me to reset it and reload 10K+
songs. (I only use the iPod for music.) The reloading process was of course a
slow and painful one, with perhaps 10 or so interruptions where a file could not be
read. But I could always pick up again. Now, it seems that all songs but one have
loaded from my iTunes library to the iPod. (I keep getting a message that the iPod
cannot be resynched because there are two songs with the same name or some
such thing. Any idea what that is?) Anyway, it keeps chugging away and finally
says synchronization is complete, okay to eject. So I eject, wait until the do not
enter is gone from the screen and detach the iPod. BUT, none of my new play
lists are there. So, I reconnect the iPod - changing nothing in the folders in
iTunes - and the iPod resynchs again, deciding it needs to reload something like
1000 songs. At first I thought maybe the time on the iPod was bad, but I checked
and that was okay. So, I am at a loss as to what to do next and would greatly
appreciate any suggestions.
One other aside question - if this iPod is permanently fried in some way,
could I just buy another iPod, hook it up to my PC, and load it with my iTunes
library. I would like to think the answer is yes, but I wonder if there is some
serial number tracking or something that goes on.
Thanks for your time. Cordially, MZ

Answer 1

Later found some other commentary on the -69 errors and disk recovery. The comments were helpful, but my 5year old iPod was beyond hope.