Newest iTunes problems

To keep it really simple for you guys, my iTunes freezes when I try to open the newest version. I've let the program sit and waited to see if anything happens but nothing does. So I finally got fed up with that and I installed the oldest version I have which is 6.0.4 or something like that on the cd that came with my iPod. I installed the program and everything seemed to work it loaded, played music and conected with my iPod but when I try to update my iPod I get an error saying " Unknown (-69) " and it stops copying my music. In the end I have only been able to get about 79 songs onto my 30 GIG iPod!
This has been a problem for me for the past three weeks. If you would kindly help that would be very much appreciated so I don't have to go out and purchase a different kind of mp3 player.
Thanks for your cooperation.

+To keep it really simple for you guys, my iTunes freezes when I try to open the newest version. I've let the program sit and waited to see if anything happens but nothing does. So I finally got fed up with that and I installed the oldest version I have which is 6.0.4 or something like that on the cd that came with my iPod. I installed the program and everything seemed to work it loaded, played music and conected with my iPod but when I try to update my iPod I get an error saying " Unknown (-69) " and it stops copying my music. In the end I have only been able to get about 79 songs onto my 30 GIG iPod!+
Both of those problems taken together are suggesting a problem with a corrupt content file in your iTunes library. With the 6.0..4.2, it's just causing the sync issue. With the later versions it's causing a hang during the "library update" phase after you've installed the new version.
Try applying the techniques from the following document:
iTunes displays a -69 error when syncing iPod
If you get the -69, fixed, try another 7.4.x install. Does the library update go through without the hang this time?

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