“ One day, I’d like to design a truly modern, functional city with the character of a medieval hill town.” This may be an oxymoron…
By definition a medieval hill town wasn’t designed: it just grew as different people built homes as best they could at the time, guided by geography, terrain, water sources etc. Chaos from a City Planner’s point of view.
Central Planning never works well, at least not as well as a free market population making individual free decisions does, but anarchy doesn’t work all that well either: the only people who actually want to live in a medieval hill town are medieval peasants.
We want all modern conveniences integrated into our homes: if they end up “organic-looking” all well and good, but they must function well and be affordable. My home is more or less a box, but I get the organic living environment on my back yard.