Anybody know about creating an entire stylized city?

I’ve seen some tutorials out there for creating realistic cities, like this one: https://www.youtube.com/watch?v=R1ROxTnD3E0
But if one wanted to do this with buildings that were heavily stylized or unique, is there any specific way you’d have to go about that, or is it just gonna take some good ol’ elbow grease?

You can create bunch of custom buildings and use Animation Nodes or Sverchok or combination of both to vary those over a predefined topology or generated topology. If not techie, you can do some distribution stuff with particles, dupliverts (or instances) and array modifier.

Next level is Python, it is basically doable with various options.

There might be some city addons too but I never checked them, maybe try making a search here on the net.

Make 2 models: 1 wide box, 1 tall box. Select them both. CTRL+G to create a group. Name it “buldings”
Create a plane. Select it. Emit HAIR particles. Emit 10.
Go to rendering tab on the particle system, choose group. Choose “buildings”.

Light and render.
Hairs will get your instances around the object. WHY HAIR?
Use weight paint maps to create (paint) where you want the buildings to be filtering by DENSITY and choosing your weightmap name.

And a looong technical explanation, which I am sure if you do these previous steps, you´ll ask and then everyone in the comm will be happy 2 help as well.
Show results.

Cheers.

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Scenecity helps do exactly this but isn’t free!