I bought the system in October 2000 but it was really a Christmas gift--it sat in my parents' closet for about two months.
Started out with Sonic Adventure and Crazy Taxi, which had both his the $20 "All-Stars" line at the time, plus a pre-owned copy of "Carrier" which was a freebie for buying the console. Wasn't crazy about it, but it wasn't downright awful either.
The console, its games, the community surrounding it and the developers that supported it were the last bastion of real magic and excitement in this industry to me, and when the Dreamcast died, so did a part of me, as dramatic as that sounds.
Here's this super forward-thinking platform being supported by some of the best, most innovative, most creative games the industry had seen and it only managed to stick around for about three and a half years.
Yes, I know a decent chunk of Sega's problems of the Dreamcast were on them, but I felt like Sega was really putting their all into the Dreamcast, and if that much talent and originality isn't appreciated by customers because they're swayed by Sony's marketing dollars, then man that's a hell of a bummer, a feeling I later felt with Nintendo and the Wii U.
After the Dreamcast lost support I moved back to PC Gaming and my GBA and more or less skipped out on the rest of the sixth generation, only returning to consoles when I bought a Wii in 2008. To this day I haven't owned a Playstation because of it.