Multiple iPods, one computer. How best to manage them?

My future brother-in-law now has, thanks to Christmas, two new iPods where he had none before. One is a 512 meg Shuffle and the other is a 20 gig 4th generation HP iPod, and he needs to manage them both from the same computer (currently an HP PC running Windows.) Since the two are radically different in terms of capacities and capabilities, having iTunes set to treat them both the same seemed to me to be a non-starter last night when I was helping him to get them set up. The solution I arrived at was this:

1. Set up two playlists, one for each iPod
2. Set the iPod preferences in iTunes so that the iPods are manually managed.
3. When he plugs in the Shuffle, go back into Edit: Preferences: iPod and change the settings there so that it’s automatically updating from the Shuffle’s playlist. Then update. Then set it back to manual management in the iPod preferences in iTunes.
4. For the 20 gig, same thing except that iTunes is updating from the 20 gig’s playlist.

He’s a professional workout coach and personal trainer, so he really wants to keep both as both are great for different things (the Shuffle for while he’s working out, the 20 gig for while he’s in the car, etc.) but there has to be an easier way to manage this. Has anyone worked out a better way, on either the Mac or the PC (he’s a potential switcher)? If so, let me know in the comments.

Update: Apparently, iTunes is capable of handling multiple iPods automatically. Thanks to MC Brown and Sam Pullara for letting me know about this, it’ll be a big help! Sam even provided a screenshot of this in action:


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