I remember my buddy had a diamond rio or somthing similar, was a pain to get MP3s on it lol.
I convinced my parents to buy me a CD burner for my birthday probably around 2000/2001, I remember it was a "PINE" brand from Costco I think, was like $450-$550
Parents splurged because I convinced them I could make CD's for friends and sell them to them lol. Ended up taking so long to burn only ever made my own mixes and occasionally charged someone for one if they heard it and wanted it lol