Syncing problems won't go away

I have an annoying problem with my new computer. Whenever I want to add songs that I purchased from itunes to my ipod and connect it to my laptop, it requests I choose to erase and sync or to add my ipod songs to my library, either way it's a disaster. And it goes through all of my 700 songs just to add my few purchased ones. Which still doesn't always work. Trying to upload cd songs onto my ipod is a nightmare too.
I am sick of this, I have been dealing with missing music (My library is totally empty) and this syncing problem from the moment I got this laptop.
PLEASE PLEASE PLEASE HELP!!!!!!!!!!!!!!!!!!!!!!!!!!

I've been trying to syncronize my Ipod with some new music uploaded into itunes and it keeps prompting me with the same message "attempting to copy to the disk "VICTOR JAV" failed. An unknown error occurred (-69).
Is there something else that i need to do? I tried to restore the company settings but its not working either. Could you please provide me with a solution since it is kind of frustrating.
On the other hand, How can i upload movies into my iPod? never been able to do this.

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