"are you sure?" message scares me but think I need automatic update.

Hello forum Im new here and about 10 of my questions have been answered by searching. However I have not found an answer to this one:
I paid for a music video from itunes, but I cant click and drag to my ipod. I saw another question like this and someone said turn on automatic updates. However, I spent alot of time putting music into my ipod manually and stuff. And when I click on automatic it says that it is going to REPLACE CURRENT CONTENT WITH STUFF IN LIBRARY. WHile that "might" help my one video to get on the iPod I think it might undo my work at getting my music how it is.
So are we saying the only way to get videos you paid for within itunes to the iPod is by enabling automatic updates? Cause right now I go to preferences and all the video selections are greyed out. What the heck?
thanks if you know

And when I click on automatic it says that it is going to REPLACE CURRENT CONTENT WITH STUFF IN LIBRARY. WHile that "might" help my one video to get on the iPod I think it might undo my work at getting my music how it is.
This simply means everything on the iPod willbe deleted and replaced with what is in your current iTunes library.
Since it is your library and your iPod, nothing is going to be replaced as everything is already in your library and in your iTunes.
This message pops up when you have it set to Manual update and change it back to Auto or when you connect it to a new computer for the first time.
Again, since you already have the songs/videos on your iPod and in iTunes, not much will be different.

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