See how damn good the original iPod looks. The non-moving touchwheel and dedicated, well-built buttons haven't been matched by any iPod generation since.
2G 20GB iPod - my favorite design, almost no flaws or bugs, sold in the days when Apple and iPod meant quality. it's brand new, bought it new in box last week. it sounds better than the 5G iPod using Senn HD600 straight out of the headphone jack - crisper highs, better mids, less slurred lows. it's so old I had a tough time finding anyone who still sells a case for it, but found the iSee on clearance, arriving next week.
3G 20GB iPod - worst design ever! worst engineering ever! worst battery life ever! latest firmware still has some bugs, like it forgets my setting after going to deep sleep. all this thing is good for is a firewire external drive.
4G 30GB color - a much needed improvement, notable for the color screen and photos, but not much else. well, maybe except for the distortion issue (though I've never experienced it).
5G 50GB iPod - if it had the buttons like the 1G/2G iPod, it'd be my favorite design. i'm not that big a fan of the click wheel, especially with Apple's in-house wheel that doesn't feel good compared to the old ones. the firmware is still full of bugs, which Apple will fix in late 2006 with the 6G iPod
iPod nano 4GB - everything about it is perfect about it except battery life (and the butter soft scratch-magnet plastic). flash memory and it still can't get 10 hours of battery life in real use.
I can't bring myself to sell the 3G and 4G because I'd end up losing money compared to what I paid.