The list of books was welcome, and the work is impressive. I always made do with section pad and a hard pencil and a simple stencil, but it wasn't for camera ready publication use or anything. Just visualisation and discussion.

My book suggestion is more illustration than technical drawing but still has a 1940s/50s vibe: Thinking with a Pencil by Henning Helms. Covers illustrations, tracing, tables, maps and diagrams as well as 3d sketches.

I gather that Tufte was influenced by John Tukey's 1977 book Exploratory Data Analysis which introduces the box and whisker plot, dot plot and so on.

As to software, another poster has mentioned Tikz (usually used with LaTeX) and yes it is amazingly flexible and can produce just about any kind of plot (or diagram) you want. But there are older tools such as the groff (GNU Troff) system's pic and a pre-processor for pic called grap which is much more barebones. The latter was also influenced by Tukey's book. The groff/pic/tbl/eqn/grap install is something like 30Mb and it is available in most Linux distribution package repositories.

https://www.lunabase.org/~faber/Vault/software/grap/example/

Oh and remember star charts for astronomers! Many hand plotted before the photographic surveys were produced. Norton's Star Atlas is a famous one (prior to the 2000.0 epoch edition) that was hand drawn.