Starting with a convex pentagon P, we define the "middle polygon" Q, whose vertices are the middle points of the sides of the initial pentagon. The ratio between the areas of this polygons seem to always satisfy:
1/2 < area(Q)/area(P) < 3/4
The lower bound is easy to obtain. I don't see how to get the upper bound.
This problem is equivalent to the following one. Just forget about the middle polygon for a moment. Start with a convex pentagon and consider also all his 5 diagonals. You will obtain a central pentagon. Prove that the area of the new central pentagon is less than the sum of the areas of the five small triangles which have a side adjacent to the sides of this central polygon.
Best Answer
I used qepcad to compute that the intersection of the set of possible area ratios with the interval [1/2, 3/4] is (1/2, 3/4). Since the set of possible area ratios is the image of a connected space under a continuous function, and we know the set contains (1/2, 3/4), but not 1/2 or 3/4, it must equal (1/2, 3/4). Here is a log of the qepcad session.