I guess a good question is: is there a good dynamic component that kind of does this already that I can alter the components to hack and make it do what I'm asking? Again not sure about Ruby so I may be limited to the 3d warehouse. .

@justintse said:

You might want to check out Modeleur -
https://www.youtube.com/watch?v=UXCHJTxQR1s

it's an urban design extension that seems like it might line up with what you're looking for.

That's pretty much exactly what I was looking for! Yeah it's pretty but maybe worth it. Thanks.

Photoshop/Gimp