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My guess would be that they are experimenting with the algorithm used to determine which cities are prominent enough to display on the map. As for why it changes so often, perhaps they are not changing the algorithm itself but just fiddling with the parameters in an automated fashion for A/B testing?

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It may be dependent on recent usage and search patterns. The standard search is influenced by 'hot' content, so why not maps?

Maybe they're not even experimenting. Maybe when you change something in one place (e.g. adding a landmark), it affects the layout of a whole lot of other places, too.

Except for that there are no landmarks shown on any of the examples. Looking at the maps, nothing is changing except for the cities and the placement of the highway labels.

The adding and switching of the different cities does seem completely arbitrary.

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