I have been trying to figure out the typefaces or stencils styles that were used for this 1941 map. I was thinking that it could be something like a Leroy Lettering template, but I can't find it. This appears to be handwritten, but also based on some type of actual lettering. Thanks.
This is standard architectural lettering for the period. I was trained in lettering when I learned manual draughting years ago: first, you draw baseline and topline construction lines, using either a rolling ruler or an architectural fixed rule on a draughting desk; you faintly line all the letters in pencil, often looking at a printed firmwide lettering standard (with construction lines) as you do it; if there are angled cross strokes (the e's) you sketch an angled line with your fixed architectural rule set to that new angle for each penciled-in "e". Once you're approved, you carefully ink.
When inking, you rest the bottom of your hand on a dowel suspended just above the paper height to avoid contact smudges, wrinkling of the paper from hand pressure, or skin oil transfer to the paper in process. Once the inking has all dried, you use a soft gomme eraser and remove all construction lines - if you have an area with delicate rub-on dot screens applied, where erasure of the construction lines may cause damage, you leave them - this is why construction lines are drawn very delicately.
Here is a decent list of 23 roughly lettering-like fonts... I'll leave it to you to find one you like. I can tell you there used to be two fonts available on Windows called "city blueprint" and "country blueprint" that were pretty good - but that was a long and hoary time ago. Your example's uppercase "E" cearly was influenced by either Frank Lloyd Wright's lettering style or the Sullivan lettering style he himself learned from.
Good luck and I hope this helps!
There are several differences in the characters that show that it's handmade:
There are also many similar fonts very easy to find like Halsvorsen Pro
It's made with a flat square pen:
In Illustrator you can achieve a similar result with a custom Art brush: