Movies on External HDD

I transfer my movies to an external HDD to save space on my MacBook after they have been viewed. I basically just copy and paste it to the HDD, delete from my MacBook, then re-add to the iTunes library. I have the external HDD setup wirelessly through my Airport Extreme. This all works well and I obviously don't have access to them when not on my home network.
The issue is that I do this in conjunction to having an AppleTV, and I continuously get errors reporting when syncing. It will go to sync and some of the movies will error out and say that they can't be found. When I click on show in finder they pop up just fine.
Any suggestions would be greatly appreciated as this error causes them to be removed from my AppleTV, and then resynced to it which is time consuming and slows my computer down.
Thank you

I have version 10.5.3 in OSX Lion which should be the most current.
Though one thing - I've been dragging the contents of the folder over - NOT the folder itself.
Wonder if that makes a difference?

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