Half of my music will not show up on my iPod, but is perfect on my PC

I have a Toshiba laptop running Vista that I bought last summer. A few months ago, my iPod just stopped coming on, or charging at all, so I stopped using it. I tried to use it again 2 weeks ago, and it loaded up all my music and worked perfectly, like I expected it to.
Now, I just connected it to my laptop a week ago to charge it, and when it demanded that I restore my iPod. I did this, but this started an entire Restore cycle that lasted for two days. It would demand a restoration, then demand another one, over and over again. I changed the drive letter, and that problem stopped.
But now Half of my music is gone, even though it came from CDs and plays perfectly on iTunes. When I try to load it into my iPod, it always gives me the same error number (Error -69) and it's always the same songs that refuse to load.
I tried breaking it up into smaller playlists, and manually managing it, but then I still had about 1/5 of my songs that simply refused to slide onto my iPod's memory. any help?
All of the music is in the same format, and I can't realize why certain songs from certain artists, or even entire artists, just refuse to get on my iPod.
As it stands now I have 1043 out of my 3653 songs on my iPod from my laptop
Message was edited by: RedWolf55

Now I just uninstalled iTunes 7.7 (or whatever the latest one is) and then restarted my computer, but apparently some files have been left over, because the version of iTuens that I'm attempting to install (7.6) says that it cannot install because a later version of iTunesis installed. Then it lists a Library file and says that it cannot install because a newer version of iTunes created the Library File.
Any Help?

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