Can't sync iPod on Windows "Can't find file" message

This is my umpteenth problem with iTunes since getting Vista. Can't resist sharing that.
Problem: I sync my iPod (bought it two years ago; audio and video, it downloads some of my music, shows the progress on the "bar", then it gets stuck on one song, will sit there for five minutes trying to download and then gives me the error message "Can't sync iPod. Can't find the necessary file" or words to that effect. I try ejecting my iPod and while my iTunes goes back to normal, my I have to wait for my iPod to run out of power before it returns to normal.
I uninstalled iTunes and downloaded it again and got the same result. However, the newly downloaded iTunes still kept my old play lists so maybe it was not completely downloaded even though it disappeared from my computer.
Any help would be greatly appreciated.
Thanks.

. when i plugged my ipod shuffle g1 in a few days ago itunes said the i had to restore my ipod. i did not want to but i had no choice cauz it already deleted my songs. after 5 trys it said "cant restore ipod"ipod". unknown error occurred (1418))(itunes did it by it self, i just put it in one very fateful afternoon. i spent 5 hrs on the computer and i still cant fix it) well i went to this web site to see if they could help me. i found something. it was a program for my ipod but by the time i downloaded it, it was too late. after a while plugging in my ipod "my computer" no longer reconized it as removable disk. a pop up comes up and says this device malfunctioned then my ipod disappears off the face of the earth. i would send it to the apple store but my warranty expired. bummer what should i do?!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!umm i dont think anything can work towards our problem

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