Electronically generating an engineering plan for installation of equipment, such as cable system equipment, at a work site. First geographic information relating to a first location of the work site is compared with second geographic information representing a second location of an engineer generating the engineering plan (or of a plan generating tool being used by the engineer to generate the plan) to verify that the engineer/tool is sufficiently near to the work site. A digital image of a geographic area including the work site is displayed on the plan generating tool, and user input is acquired from the engineer (e.g., via a user input device associated with the plan generating tool) relating to at least one first position, relative to the displayed digital image, representing a first equipment location of at least a first piece of the equipment to be installed at the work site. A marked-up digital image including at least one first digital representation of the first piece of the equipment placed on the displayed digital image is generated, based at least in part on the user input, and information relating to the marked-up digital image is electronically transmitted and/or electronically stored so as to generate the engineering plan.