Windows 7 Tip: 
Web site Hey!Watch lets you upload videos from your hard drive or online video sites like YouTube, then encode said videos to nearly any format on the planet, including pretty much anything you might need for a portable device.
One of the most brilliant features of Hey!Watch is that they create a podcast feed of your converted videos, meaning you can, for example, add your feed to iTunes, which can then automatically download your converted videos and sync them to your iPod. The only downside (there had to be one for a web app this cool): Hey!Watch only allows you to encode 10 videos/month, along with a few other limitations, unless you pay for the $5/month upgraded plan.
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