Haha, where to begin...
I started out with a used Apple IIe from my school, and then in 1994(har har) I upgraded to a Quadra 605 (I had three of them in fact, I'd end up putting so much crap and games on one, it would fill up and I would need another one
) Those were winners... 25mhz processors, 32mb RAM... 4x External CD-ROMS... those were the days. Then in about 1997 I bought a used Performa-something I don't really know, 90mhz 64mb 8x CD 1mb V-RAM (That was the kicker) like, a 2gb HD (NOT Apple, it was custom)
So up till then I had been in the world of OS 7.1... ish...
Then in 2000, I bought a Rev D iMac DV Slot-loading (My beautiful indigo baby) 500mhz G3, 320mb PC166 SDRAM, 16mb RAGE128 24xCD... It was a thing of beauty... So, of course, I wanted more... I found a couple more just like it and bought them.
So as of this point, we are up to 8 Macs....
Then comes the summer of 2004... When I bought my drop-dead-gorgeous iBook G4... 1.2ghz, 1.25gb pc2700 DDR, 60gb HDD, 32mb ATI 9200, and a combo-drive...
So, all in all, I've owned 9 Macs... Each one of them is operational and as useable today as it was when I bought it