My back ground, Autocad user 40+ years, Civil Engineer, last 17 years, Design Unit in one of Australia's largest Council. Reaching team leader of the design unit, 8 designers, multi millions budget per year, largest personal project $12 million. Years of GIS vector and image out, to Autocad.
I am currently semi retired just doing training and customisation of Acad and Bricscad.
The creation of paper space layouts along a pline has been discussed many times and is available as free software just a case of finding the most suitable version for you. Various methods like overlap, normally would follow pline angle and twist to suit, but easy to convert to ortho view only.
So solved problem 1, looking at pdf really need to know what you think you would automate ? Layouts could be created with some form of rules overall sheet1, gen notes, linetypes, then layouts at scale.
How are your existing sevices imported we had the advantage of drainage, water and sewer exported from our GIS, electricity and gas, were hand entered is that something you need sped up ?
I am located in Australia, near Sydney. Where are you in the world. Is it Louisville USA.
Please email info@alanh.com.au and we can discuss further.