My iPod is annoying me. Can someone help before I throw it out the window?

Here's what's happening:
1)I was having some trouble with my iPod and I restored it with the newest iPod Updater. Then uploaded my songs. The only songs that worked were the ones I imported from CD's.
2) Then I downloaded the newest iTunes and and updated my iPod again. Only a few songs didn't work this time.
3) But now whenever I plug in the iPod to update it, it says I have to restore then update it. I must have done this 2 or 3 times by now. How do I stop this from happening?

Here's what's happening:
1)I was having some trouble with my iPod and I
restored it with the newest iPod Updater. Then
uploaded my songs. The only songs that worked were
the ones I imported from CD's.
2) Then I downloaded the newest iTunes and and
updated my iPod again. Only a few songs didn't work
this time.
3) But now whenever I plug in the iPod to update it,
it says I have to restore then update it. I must have
done this 2 or 3 times by now. How do I stop this
from happening?
Now my click wheel's acting weird.
Windows XP

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<Personal Information Removed by Host>

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1) You are using iTunes 6 here, correct?
2) You did not say whether or not you are running in auto-sync, manual management, or "Enable Disk" mode. If you left it in the default mode as installed (auto-sync), then after dropping your movies into iTunes (or adding them to the Library), simply connect your iPod and allow it to auto-sync (mirror) the current contents of iTunes. (You can also try "Update iPod" option under the File menu, but I have found it unreliable -- possibly owing to "sleeping" iPod.)
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My iPod is annoying me. Can someone help before I throw it out the window?

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