I got started the "old" way too, in the early 90's. We had a large FLEET account that was reflective vinyl. The owner made templates and I would trace them to the vinyl with stabillo and hand cut them. The letters on the trailers were large, single color but the cabs had an outline and the smaller word "Transport" was only about 2.5" and in an Old English style font. I'd trace and cut the letters and then nest them on the second color and cut the outline. It was boring as hell but it sharpened my skills, I'll hand cut a lot of stuff to this day and people look at me like "how (or why) did you just do that." For painting, he would lay out everything quick & rough with a stabillo and we would go to it with the 1-Shot. At first, he laid out what I was to paint pretty firmly and as I got the hang of it, his sketches loosened up and eventually I was able to lay it out by myself. We did a lot of race cars & little league 4x8's. I don't even have any photos because it didn't seem like anything out of the ordinary to photograph (plus we didn't have a camera on our phone... or a phone at all... in our pockets). I still use paint quite a bit but almost exclusively pinstriping & custom painting.
The talk about heights reminded me of one particular story when we were painting an "AGWAY" logo on a large fuel tank. The restoration company had already coated the tank and left us their "spider." A cage, about 3x8 hanging from the top of the tank by ONE wire. When he moved, I moved and visa-versa. There is no amount of money that would get me up in that thing today but I didn't really think much of it at 18.