Crap. Old enough to have used all those things....probably says something about the pace of change accelerating or something.....
When I first started in 1977, it was required to use chains to measure things out, the thought being that new fangled cloth would stretch up to maybe, I don't know....a 1/16th of an inch, which COULD throw off the entire design. LOL.
The pointy thing in his had could be either a compass for drawing circles, or calipers for transferring distances from one point of the map to the other.
Of course, I learned to draw with T Squares. Coincidentally, I just moved one into to my new attic while straightening up today. Saved it all these years for some reason. Sometimes helps cut paper at right angles.
What they don't show there is the Plane Table, a table a bit smaller than shown there, with a transit attached on top. Thus, you could set up on your control point, set the transit to whatever angle you needed to aim at a staking point, and it would automatically give you the angle, without measuring. The University of Illinois had one and we trained on it, but I never used on in practice.