1) Sony boombox with a CD player (1989)
2) Sony Discman (1993) (this led to a solid move from cassette to CD's)
3) JVC CD player (part of my first "component" system with JVC receiver and PSB Alpha's) (1994)
...then comes University graduation, followed by full-time work and pay, which led to the next stream...
4) Marantz CC-3000 5-disc changer (2000)
5) Bel Canto DAC1 added (2002) (still using Marantz changer)
6) Meridian 506.24 (2004)
7) Ayre CX-7e (2008)
...and that should be it for quite a while now...I don't change components very often relative to most on these boards, but when I do, it's generally for clear improvements. The smallest improvement was Marantz/Bel Canto to Meridian - that was more of a sideways step compared to the rest, which were all easily audible changes. But the Bel Canto to Meridian change was caused by necessity - had to move overseas and didn't wanna bring the stereo equipment with me due to transport issues.