This is an awesome thread. Quality build too.
I have almost the same timeline and story you do. I fell in lust with a 60s American car, bought it in 1999 while in High school (with help from parents of course), went to Auto body school in 2002 and worked on it there much to the dismay of my somewhat burned out teacher. I had a great time in school but never had much luck in the business after graduating. I don't do bodywork professionally anymore but still do my own stuff on occasion.
I still have the car too from back then. And over the last couple of years have been working hard to correct past mistakes on it, including an axle ring gear swap to a higher ratio just last week.
Keep the posts coming!