As a recent (6 mos) iPod convert and a recent Mac Mini buyer, I would vote for the iPod. I've had Rio's (2) and Muvo's (2) I strongly believe iTunes has done it right. W/ yesterday's addition of podcasts, it makes it even better. Especially if you like to listen to lonely geeks pontificate in the basement of their parent's houses, since this is pretty indicative of the majority of podcasts I've sampled... But the good ones are just that, good ones.
That being said, I would recommend Peter's suggestion of using the iPod as a hard drive rather than loading it via iTunes. He can then personalize it himself. Go to ipodlounge.com and you can see various people doing the same. Also on Apple's site there are user forums specific to the iPod that address this same question. A similar situation came up when I tried to move my MP3 library from an XP machine to a Mac but still preserve my playlists. My library, btw, is about 35 MB.
I agree w/ input about gapless playback. That is one thing that really bugs me. So, I still buy CDs when I really want to have an audiophile listening session, that way I don't worry about gaps and compression.
The new 20GB iPod color is only $299, same price I paid for my 20GB in December. [sigh]...iPod upgradeitis...
