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Earlier quoted context omitted.
There's other things to look for. Are they driving on the left or right? Is the road dead straight (if so maybe Australia/USA?) Is the road line down the middle yellow (USA and I think SA) or white? etc.
Makes of cars/trucks are another thing - North America is pretty distinctive.
It should help to know that streetview is only available in North America, Brazil, Europe, South Africa, Japan, Thailand, and Australia.
Tougher than it seems. It's not so bad when you're in a city and there's some kind of writing and architecture, but often as not you're in the middle of nowhwere and it's all guessing based on rocks and trees.
Challenge mode: Leave the guessing map at default zoom. 20 minutes or less. http://bit.ly/1a4y8Ne
Great game. Maybe include some kind of URL shortner for sharing? Those URLs are quite massive.
Australia, man - gets me every time (at least when there are no visible cars driving on the left)