The iTunes converter really sucks - I don't recommend using it. At least for Windows.
I use the
Videora iPod Converter to convert movie files to MP4 that I download from just about any format. Super easy and free.
And here's their tutorial:
http://www.videora.com/en-us/Converter/guides.html#1000 I've also had good luck with Nero Recode, which is free for Nero users, but others will have to pay. It's faster then Videora, but I recommend qeueing up Vidoera and let it run over night and all of your movies will done by morning.
Or you can pay $30 for Quicktime 7, but it doesn't convert as many file types as Videora.
If you want to rip a DVD, google DVD Decryptor or DVDFab Decrypter.
Spend a lot of time here too:
iLounge: Filling your Video iPod Forum Last suggestion: buy the base and hook up the Video iPod up to your TV with an S Video cable. The quality is fairly impressive.