Hi all, first post here. I'm 29 years old and have been playing CB games since sim city 2000. I've played over a dozen - the Caesars, the other Roman Empire games, Europa universalis and its ilk, Egypt themed city builders, Chinese, u name the historical or current CB and I've mastered it.
I have been waiting this whole time for a non-fantasy, non dragons-and-golems medieval cb. Here is my take on the grid issue.
In all the games I played, I've had to build cities in a grid pattern with streets at 90* angles to each other. The buildings too were in a fixed shape that would not fit properly unless the street were perfectly straight. This is annoying because u build entire cities on a neat little grid pattern. This makes everything to orderly an artificial. We ALL know that roman cities were pre planned on a grid, but other cities ESP during the medieval era (even medieval CITIES not towns that were initially roman settlements) eventually lost their grid patterns and the streets took on new, messy, meandering shapes. Look at Paris. The City of London. The city centers or oldest part of most European cities, when viewed on maps or better yet aerial views, have spidery, crazy looking streets.
The streets go in any direction and the buildings cling to the streets. If any potential "realistic" medieval CB is to be credible, an ability to build meandering streets of various widths and directions is necessary and more importantly to have non-fixed-shape buildings.
Even in modern art depictions of medieval towns (one can google these images) the artist draws a clustered jumble of buildings with streets going in any and all directions and shapes.
Fluidity of street shapes and the ability of buildings to cling to streets instead of fixed-shape, 2x2 square bldgs is necessary for Medieval Mayor to seem most real.