Microsoft just needs to search for already available imagery from the providers and purchase the right ones. If you check Google Earth’s historical imagery for a given location, you can see many cloudless images for these areas in their archives from public sources. No need to fly a custom aerial flyover. Microsoft probably already has a contract with such providers and only needs to request the ones they need as part of their subscription. That’s the way Google does it for their imagery (I blogged about Google Earth for a while).
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