The 8bit maps joke is especially interesting to me for one particular reason: it draws attention to the fact that certain things are much easier to see in low resolution than high resolution. For example, if you zoom out, it's much easier to get a general idea of the location of major mountain ranges and deserts. The Terrain and Satellite views, by comparison, are much more detailed but much less obvious.
Zoomed farther in, it's much easier to make out the general pattern of major roads in the 8bit view. This is a bit more dubious since clearly what it's showing is only a very tenuous view of reality, but it reminds me of one of the big innovations I read about in subway maps: the idea of not drawing them to scale. In general (although NYC seems to be mostly an exception here), subway maps show stops as mostly equidistant, which makes them look a bit nicer, but also more closely reflects the reality of a subway (most of your time is spent sitting at stops, so in fact, stops are pretty close to time-equidistant even if they're far apart physically).
That, in turn, reminds me of my grade 10 geography class, where the teacher talked about drawing a map of the world where each country was scaled by population instead of land area.
Which then reminded me of another of my friends who once drew a map of Toronto scaled by transit accessibility; that is, it was drawn larger and in more detail near subway stops, and smaller further away, which works well because there tends to be more density of information near transit stops (since there's a higher density of services).
Anyway, I like it. And I'd love to see a special variant of maps that drops out all the annoying details, including the squiggliness of real-life roads and listings for businesses I didn't ask about, and just lies to me about how to drive to my destination, in a way that actually makes it easier to navigate. Probably I'm the only one who would like that, though, which is too bad.