Error (-69) attempting to download purchased video content to 160GB Ipod

I am attempting to download purchased video content from Itunes to my Ipod. Till recently there has been no problems. I believe this problem is actually stemming from the downloading of content to my computer resulting in faulty files that cannot be downloaded to my ipod. I am using a Dell XPS desktop computer running Windows XP Media Edition. All software relating to Itunes or my Ipod is up to date as of the writing of this post. My Itunes library, music and video files are downloaded to an external Hard drive rather than to my desktop because of the massive amount of data. As of about two months ago I noticed that many of my songs (about 1 out of every ten and many of which had been fine for months prior) was in some way corrupted. However my Ipod still has many of these same songs that work fine. Sooooooo. First- How do I replace individual songs or at the very least download all music and selectively delete duplicates. And Second- figure out what is causing BRAND NEW video files to download messed up. Any advice would be helpful. Thanks

See this trouble shooting article.
iTunes displays error 69 when syncing iPod.

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