I credit my developing an eye for identifying typefaces to my use of The Print Shop at my public library when I was in elementary school. I don't know that I was aware of the idea of typefaces before that.

My junior high had signs, printed in The Print Shop, announcing administrative minutiae and offering "pep talk" slogans. I'd scratch down the particular combination of typeface, border, and clip art they used then print subtly different replacement signs I'd hang over the originals. It went on for awhile before I got caught sticking one up. (I was particularly pleased with replacing "All lockers are school property and may be searched at any time" with "All thoughts are school property and may be controlled at any time".)

As an aside: The Print Shop Companion on Apple II has a hidden "driver" game on the B-side. You press ESC then CTRL-SHIFT-6 to get to the game. That was one of the first Easter eggs I'd ever seen and I remember having a feeling of wonderment at the idea that secrets could be hidden in software.