"Convert Selection for iPod" Command Increases File Size?

Hello!
I'm trying to convert a file that has the following characteristics (as reported in Quicktime Pro):
Format: H.264 Decoder, 496 x 208, Millions, AAC, Stereo (L R), 44.100 kHz
FPS: 25
Data Size: 572.20 MB
Data Rate: 659.18 kbits/sec
Normal Size: 496 x 208
I know the dimensions are strange, but it's because this is just a test I'm running on a workflow using Hand Brake to bring content back from a DVD (my content).
Now, when I drop just the original file into iTunes and then try to put it on an iPod, it says it can't be played. So I use the handy new option in the Advanced menu, "Convert Selection for iPod." This yields a new file with the following characteristics:
Format: AAC, Stereo (L R), 44.100 kHz, H.264 Decoder, 640 x 268, Millions
FPS: 25
Data Size: 1.36GB
Data Rate: 1609.01 kbits/sec
Normal Size: 640 x 268
How is it that the data rate and file size have increased so much? It now plays on an iPod, but why? I was under the impression that usually the problem with getting video to play on an iPod was a data rate that is too high. So it seems strange to me that the second file works and the first doesn't.
Finally, what is the difference between a file with the extension .mov and the extension .m4v? The original file has .mov and the converted ends up with .m4v. But they have the same characteristics in terms of codec. So what's the difference?
Thanks for any help and info!
Cameron

I think I was able to resolve this myself after some trial and error. It looks like it is all in the name of the file. I've gotten some files to transfer after going into the Get Info section and updating the name (usually shorten the name or take out non-letter/number/# characters and then get the filename on disk to match.

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