My first MP3 player!
The Rio 600 is the most ergonomic device I've owned - it feels wonderful in my hand. The belt clip makes it really convenient to carry. It synced with SoundJam MP on my iBook G3 using USB, which was brand-new when I got it for Christmas 1999. My first one was stolen in Pisa, but I replaced it. It continued to sync with iTunes until version 7, due to drivers from SoundJam that Apple removed when Palm started using them. It had only 32MB, and held only 8 songs, so I got tired of the music quite quickly. But it was perfect for making a digital mixtape, and giving it to a girl I liked in 2006. Battery life was also good, and the AA battery standard was very convenient. I eventually replaced it with a MiniDisc player, before upgrading to the original iPod in February 2002.
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Also props to minidisc..
It was credit card sized and very thin, had a robust aluminium cover, 128mb storage and a connector similar to that of an iPhone 4 which connected to the serial port and as far as I remember it was not compatible with anything but the odd file transfer application it came with. Other than that a great little gadget whose proportions and functions would amaze people back then. I also ended up switching to an MD player for the superior sound quality and ability to carry more music around without slowly transfering files over com-port.
I've skipped the portable CD players, going directly from portable cassette players to this mp3 player. Afterwards I went through a bunch of (near-cylindrical) iRiver mp3 players, whose joystick always broke after one year of use. Here in Europe that meant free replacement every year, which wasn't bad at all.
Now I just carry my Samsung Galaxy S4, with an 64GB microSD card and Google's All Access...
By the way, your timeline is broken, the Rio 600 came out Q2 2000, not in 98 or 99. The very first Rio 300 was released in on 9/98 and the 500 9/99.
My first portable music player, ignoring years of walkman-clones (never had the real thing!) was a Minidisc player - the Aiwa AMF5. This was bought with my first year's student loan money and lasted me till the third year, constantly in use, constantly naming tracks and discs with the jogwheel. It was a great technology, so when my F5 got a bit bashed up I upgraded to a secondhand AMF65, but that was never as reliable - I guess I found out why it ended up for purchase in a Cash Converters. I backed it up with a Sony MDS-JE520 MD deck for my hifi to make MD creation a little easier, and naming tracks faster with a one-button-per-letter remote control.
Onto non-mechanical devices, I "borrowed" an ex's Creative media player - it took SmartMedia cards (I think it was SmartMedia - the credit-card-flat ones with the large contact area on one end). 32MB meant about half an hour of music, and USB1 meant about half an hour to update the thing! It didn't get much use and I pretty much forgot about portable music for a while since it wasn't really convenient. I did however get a Motorola A910 Smartphone which had an MMC card in the bottom - 128MB that could be used for music, so to some extend that took over.
From there, I changed girlfriends and "borrowed" her Creative Zen Touch - 20GB on a hard drive. I still have that, although the contacts on the back of the touch area on the front have died, so I got another with a dead hard drive and one day, for old times sake, will probably make a working one out of the two.
That was the first useful one, and perhaps the last - by this time my A910 phone had been swapped for an HTC Canary, with SD card access and therefore much cheaper storage. a 256MB card was purchased, loaded with music, and I found the joy of only needing one device in my pocket.