Haha. I myself tried to play CS like that. Start with a historical core. The thing is the way the game is implemented buildings only have rectangular footprints while in reality buildings occupy the spaces more organically. I actually spent quite some time on google maps trying to see what pattern historical buildings followed to fill in spaces but couldn't get a definitive answer. I drafted it at some point in sketchup. Here is the result

https://imgur.com/a/procedurally-generated-buildings-that-or...