You can use a scaled grid system. If the printed letters have a grid of say 1/8″ inches and the corresponding street grid is scaled up to say 3 feet and each large square contains the same content as the smaller square you’ve enlarged the text (or any other image content). The grid can be drawn on the street with rulers and chalk (or the afore mentioned surveying tools and lasers) and then the image transferred and paint applied.
This can be accomplished with the use of surveyors tools and good measurements. You can basically pick a font and scale it up to the size of the street. Surveyors tools, like laser distance finders, can help you find all the vertices. Then you use a guide line (string between the points) to either paint or mask.
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