Yeah, I said in a previous post that I’d used SpecialMeshes to do similar work to what I’m doing now. I’ve easily scaled these to tens of thousands of studs large to create seemingly endless oceans, too! 
More or less, yes. The main terrain will be created by a plugin I use for Blender, and then I’ll be modelling every house and airport by hand. The buildings won’t be too hard, as I’ll be using very simple shapes with a decal / texture applied.
It’s going to be a flight simulator, with a wide variety of aircraft. I’m going to shrink the map by a huge amount, so to the player it won’t feel too different from a 1:1 scale map. I was planning on using the up-and-coming Dynamic Skies feature, though that may not work too well with the scaling.
Edit: I am now working on a prototype for the game’s terrain 
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