Can't get purchasedE video onto Nano even after selecting Advanced convert

I have a new Nano and have purchased 5 short videos from iTunes store. Firstly, when synching the error was "cannot be copied onto this iPod because they cannot be played on this iPod". I read in the forum that I should try selecting Advanced and then convert to ipod. When I do this, I get "Error occurred when converting. Unknown error (-3000)". Any ideas where I'm going wrong? The 5 videos were all purchased by me from iTunes store. Is it anything to do with the age of my mac? Thanks for any help.

Your first error happened to me this morning when I was using the iTunes on my computer for my boss's ipod nano. I has to go under Store/Authorize Account and then just followed the prompts. Now my problem is that I cannot see the movies that I purchased from the iTunes store on my ipod. I can see them in iTunes when my ipod is plugged in, but they are greyed out.

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Can't get purchasedE video onto Nano even after selecting Advanced convert

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