As for me, I am still dreaming about a smart, simple & straight forward WebGIS with endless layers from a world-view up to a local 1:5000 level that may be customized with an API. Similar to GoogleMaps, but much better georeferenced.
Oh, and I like this timeline above. Agree with the placing of the current maps ease-of-use status because there may already be services like http://www.mapbuilder.net/ but anything advanced still requires some coding.
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