
Rule 1: Encode everything at a bit rate of 192.
Rule 2: Don't buy anything from the iTunes website unless its iTunes plus - anything that kills freedom and responsibility is beyond me and Digital Rights Management is vile. And stick to MP3 as a format.....don't get locked into Apple's proprietary format or the DRM version of MP3.
Rule 3: You need to buy something to normalise the volume of tracks across your collection. The best free software to do this is MP3Gain. Tip: stick with the default volume settings on MP3Gain and adjust volumes per album, not per track. Get MP3Gain.
Rule 4. You need something to boost the volume of the iPod (for those frustrated with the default volume restrictions). euPOD Pro 1.6 is free and excellent software to do this. Get euPodty)