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This is a variant on Euler's bridges of Konigsberg. In short, it is impossible if more than 2 areas have an odd number of enclosing line segments. In your example, 3 areas have 5 line segments enclosing them. Therefore, it is impossible. If there are exactly two areas with an odd number, you must start in one, and end in the other. The reason is simple. If you don't start in an area with an odd number of segments, you will ENTER it through one line segment, then LEAVE it through another, then ENTER it through a third, ... until you ENTER it through the (2*n+1)'th line segment... which means you can't get out of it any more...
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