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There are m3u playlist exporters & converters for iTunes so the playlist issue is a non-factor unless you change your playlists multiple times a day.
From there it's simply personal preference. I'm personally going to go the USB memory-stick route for several reasons:
- A 8- or 16-Gig USB memory-stick holds plenty of music.
- I won't worry about it overheating in the sun.
- It has no spinning parts to worry about on a bumpy road. (The iPod can definitely handle the bumps but I worry about some of the dirt cheap external drives people have been using for this)
- It won't need to be recharged like the ipod.
- I won't accidentally forget it - it stays in the car while the ipod comes with me.
- If someone breaks into the car it's much cheaper to replace than an ipod. They might even ignore it - who wants to steal a USB memory stick?
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