Windows (AIR 2.0): HandBrake is our favourite media converter and DVD ripping tool. DropFolders automates HandBrake slightly, having it watch a folder, convert what it finds and drop it wherever you'd like.
DropFolders relies on the native code capabilities of Adobe's AIR 2.0 platform, and it's a great use case for them. The app interacts with HandBrake through its command-line interface, so you'll need to be up on the lingo — but only just slightly. Since DropFolders handles the file input/output commands, the only presets you'll need to set up are the encoding parameters. HandBrake's own CLI guide shows that, rather than typing in archaic variables, you can usually get away with entering something like
—preset="iPhone & iPod Touch" or any other preset name that HandBrake understands. We're wondering though — would this work with iTunes' automatically watched folder?
So it's not exactly a beginner's tool, but DropFolders does automate some of HandBrake's powers for you. It's a free download, and it may also work on Mac or Linux too — let us know if you've given it a try.