I always thought the sync-cable-doubles-as-power-cable thing was so ingenious. Could you charge any product over USB at the time? I don't remember anyone doing this before Apple did, and it helped that the FW400 cables were the same on both ends. And on top of that, all of the chargers were modular in the way the Macbook chargers still are today; you could swap on the "long cable" end in place of the flip-out prongs, or use the non-North America travel kit tips with any of their chargers as well.

I was sad the day the iPhone started shipping with just a simple USB->power brick with the modularity removed.

This is anecdotal, but maybe it'll explain a bit more where I was coming from in regards to my reaction to the initial ipod reveal. Back then, my music player adaption went from CD Player, CD Player with MP3 CD support, to Nomad Jukebox 3. Size was not an issue at the time, since I was used to the CD player size and was more looking for ways to get rid of all the CDs I had to keep bringing with me. The Jukebox 3 had the largest HDD at the time, as far as I recall, and allowed me to put my full CD collection on it at that time already. It was also running on a larger battery brick and had an additional slot for another battery to extend its playtime. The batteries were charged in an external charger, so that you could simply swap out the batteries and keep on taking the player with you. It also came with a remote control, which was more of a gimmick, but came in handy every once in a while. The UI allowed browsing through a scroll wheel on its side and you could access the music through various ways (as far as I recall: genre, artist, album, song, and playlist). Especially the scroll wheel was so easy to use compared to the click wheel on the ipod, which appeared to be more gimmicky than useful at the time.

Of course, by now things have changed and I love the fact that I can put all that music on my phone and being able to connect it to all the different devices (bluetooth & audio jack speakers/headphones), so that I wouldn't want to take a dedicated MP3 player, especially the size of the Jukebox 3, with me anymore.

However, at the time of the original ipod release the lack of HDD size in favour of hardware size didn't make any sense to me and I still catch myself thinking like that during some of the Apple release events since, where it sometimes seems like they're taking one step forward and multiple steps back - will be interesting to see what happens during the upcoming Macbook event.

Exactly. Firewire = charging + super speed. iTunes was Mac only at the time, for (relatively) easy management and syncing of your music.

Yes, Jobs was short-sighted and made a bad business decision by not supporting 95%+ of his potential customer base.

He subsequently did a 180 on this decision - Gen 3 introduced USB syncing, Gen 4 introduced USB charging, Gen 5 dropped Firewire syncing - and hey presto, the iPod started selling more than 5 million units a year, started being profitable and swallowed the entire competition.

Who cared? It's not like I listened to a thousand songs every day and had to write a thousand more every night. It took an hour the first time to fill it up, then I'd only replace an album or two at a time.