When did the realistic typesetting of chemical structures start?
this isn't a definite answer but it might show the direction:

I have an old copy of Namensreaktionen in der Organischen Chemie, 2nd ed. by Helmut Krauch and Werner Kunz, published in 1962 at Alfred Hüthig. First edition must have been published in 1960 or 1961.



Most of the arenes in the sketches have the proper shape. Once in a while they seem to be deliberately stretched to align centres that react.

All through the book there's a consistent notation for saturated centres, hydrogen atoms are mostly not omitted.