How can I convert video and audio files into iPod/iPad playable formats?
HandBrake used to be my go-to app for this task but lets face it: nightmare UI. Especially if you're a professed "non-technical guy".

The new wonder-in-a-box video convert is Smart Converter. Like HandBrake, it's free. Unlike HandBrake the UI is very non-threatening. Drop file, pick output format, go. Works for video and audio.