What got me thinking about this more seriously is looking at Harvard Square's website. We've done maps for H2 for a dozen years now (and hopefully that link will take you to some newer web maps soon), and now they are a guinea pig for a new thing, "Everyscape." It's slow, it's kinda clunky in interface, but I can see a lot of potential in this sort of visualization replacing cartography for large-scale mavigation.
But.
It's all still designed on the basis of a landscape. Where I think some sort of 3D is needed is in complex indoor environments. Montreal or Toronto's habitrail environment of street-level, below street-level and above street-level navigation. You can't see beyond whtever corridor you're in, and goodness knows how that corridor relates to the whole. We deal with something similar in Minneapolis (see top image, below, but we mostly only have one level above street, and a second set of lines works graphically OK.
By contrast, St Paul's skyway system moves down a slope, so the skyways at one end of the system are a few stories lower than the ones at the other end. Not that you'd know that from our maps(see bottom image) (or anyone else's).
VR or 3D rendering ought to be able to make basic navigation in these sorts of truly 3-dimensional urban spaces work, but I haven't seen a system really do that properly yet. Tim?

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