Automatically converting and transferring video files to TP2

I just use Windows Media Player 12. I select "Sync" from the top left corner when the device is connected, drag-and-drop the files I want transferred into the playlist, and it automatically converts and syncs them over.

I used to have a much more complex system that involved scripts and fancy programs that converted the codec and size etc, but I actually find the Windows Media Player works awesome for this case.