Ahhh.. this is a writer after my own heart. Absolutely brilliant write-up. I had the same obsession with roads, from SimCity onward; they're the circulatory system of any city, and never in the history of cities or the history of circulatory systems have the vessels been straight lines. The streets of a European or Asian village usually tell a story about how roads were built over the fastest footpath from the outskirts to the center, then over time amended to go around some buildings that were built in the way. Whereas roads in rural parts where I come from run in long straight lines and then suddenly swerve to get around a piece of land that a farmer wouldn't sell. But grids only exist in some parts of the few cities that were built mostly by colonial powers, or developed later with master planning. And even those grids usually split from their original orientation to becoming north-south at some point in in the city's development, leading to the interesting downtown triangle blocks of cities like Portland, San Francisco, Los Angeles, Seattle, New York. Other cities started to grid around their core footpath villages, like Madrid, Barcelona.

The cities I find the most interesting (for roads) are the ones which kept gridding out in new directions to follow the course of a river. Cities like Buenos Aires, New Orleans, and Saigon, where the original paths followed curves around the river bends, resulting in multiple intersecting grids.

The intersections and division boulevards between grids are, of course, the most beautiful and architecturally interesting parts of any city. They are where the blocks are strangely shaped and the buildings can't be rectangular, and usually where every inch of land is at a premium as well. It would be nice if a city-builder could simulate that aspect of urban growth: The shift from village center to grid, and old grid to new grid.