My wife and children gave me an 4 gig iPod Mini many years ago, and it turned out to be one of the best gifts I ever received... It nudged me into using my computer as a music server and I immediately began ripping my CDs using iTunes.
The Mini was a great first iPod for me, because it forced me into using Smart Playlists to sync a "fresh" portion of my collection onto the device. I really like this element of the iTunes interface, and the random play features occasionally pull some obscure track from my old recordings that I'd forgotten about completely - but really enjoy a lot upon rediscovery. It helps keep my collection in front of me - rather than just the most recent stuff I've been into.
Nonetheless, I've got a very diverse collection of music and some of it does not really want to be played together randomly! So I began using groupings to provide some additional intelligence to the "smart playlists" that I was constructing. I hope that you utilize this feature of iTunes, which allows you to "program" virtual DJs to put together playlists that refresh themselves. In a sense it provides a crude artificial intelligence of sorts - and by providing a a little "feedback" you can tweak how the iTunes compiles the playlist.
I will say that I am not a fan of the stock iPod earbuds, and replaced them promptly with Shure E3 earbuds (with Shure foam sleeves), which made a huge improvement in sound quality. If you listen regularly to your iPod on headphones, good quality earbuds is one of the best investments one can make.
Well, after I wore out the battery on the iPod Mini, I bought an 80 GB video iPod - which allows me to carry a good portion (but not all) of my music collection with me.
Most recently, I replaced my Dell desktop with a Mac Pro - which is an exceptional computer for use as a music server. And I added a Sonos system to tie the music server into my house stereo as well as my new office listening system.
I'm one of those people who worry that too many young adults today have not been exposed to hi-fi sound, and don't know what they are missing. Digital music can sound like crap - but it also can sound fantastic. It's primarily a function of source bitrate, amplifier quality and speaker quality. You've got to hear the difference!
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