I am a writer/historian with decent computer skills. I am writing a book about an old city that barely has any historical maps.I would like to create a series of maps to show how the city evolved over centuries.

Do I start with a current Google Map of the city and then try to work with some tools to erase the newer structure and then juxtapose it with the older structures that don't exist today. I would like to create a medieval look to the map(s) as well so that it looks authentic.

I saw a few tutorials in here and in the web but I am not sure which is one would work for me.

Thank You for your time.