Video Syncing Problems

Hello,
Recently I have been trying to sync a 30 MB video file in MP4 format to my 8 GB iPod Touch first generation. I have nearly 6 GB of space on my MacBook and nearly 5 GB of space on my device.
Here's my problem: I open up iTunes, attach my device to the computer, and check the box of the video so it should sync. I click Apply. Immediately after, a message pops up and says, "There is not enough free space to hold all of the items in the selected playlists (27.09 GB required, 4.97 GB available) ".
My analysis of this message: It says I have 4.90 GB of space left on my device, but it's close enough to mean they could be talking about my device when they say what's available. What confuses is me is why 27 GB needs to be required when I have less than 8 GB possible on my device. Even if they were talking about the computer, why would I need 27 GB to transfer a 30 MB file?
I have tried using QuickTime to export my video again. I have tried to import to library. Nothing works. In fact, if I try and import just a playlist of songs the same message pops up. And same message pops up for photos.
What's going on? How can I fix this problem? I'm on a time deadline, so please respond ASAP!
Thanks!

Woops - manually manage box wasn't checked. Sorry, it's fixed now.

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Message was edited by: ADAMATIUM HEART

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