I started out with, if I recall correctly, a Performa 5200 or 5500. The pictures I have found online show it to be one or the other, from what I remember. I was in 4th grade and was learning to type. Last time I was at that grade school, they still had a few of them running and still in use. All through grade school and high school, we had nothing but macs. Sure, we had Windows at home, but macs were at school. Looking back, and looking at dates and such, I must have started on System 7, and later on Mac OS 8 and some of 9 just before High school. I remember when Mac OS 10.0 came out, how amazing it was compared to OS9.
Then for a while, I was using Windows 98 and 2000 at home and school, as we got new Compaqs at the library, and then returning to 10.3 for my programming class. After that, and experiencing FCP on an eMac, I decided that was what I wanted to do in life (edit video) and then went on to community college with iMacs and an old G3 running next to a GrassValley switcher.
Finally, at my internship, I was introduced to the G5 and to a macbook pro, right when the Mac Pro came out, and we then took a trip to the local apple store and purchased a 6grand Mac Pro for the business. That summer I ended up getting a 17inch macbook pro and FCS.
Amazing how computers have changed in only 15 years, eh?