In an n-sided (n>4) regular polygon, label the vertices {0, 1, ..., n-1}. For each vertex i, draw a pair of diagonals:
- from i to (i+2) mod n and
- from i to (i-2) mod n
Question: What is the ratio of the area of the internal polygon to the external polygon?
For n=5 and n=6, this process will result in the following diagrams. For the pentagon, the ratio would be area(ONRQP)/area(CBFED).

(source: uga.edu)

Background: This page has a discussion about pentagons and notes that if CB=1 (unit length) then ON=1/$\phi^2$ where $\phi=(1+\sqrt5)/2$ is the golden ratio. Since the area of a pentagon is proportional to the square of its side length (see here), area(ONRQP)/area(CBFED) = 1/$\phi^4$ ~ 0.146.
But I don't know how to generalize it to a regular n-gon. It seems obvious that as n increases, the ratio approaches 1 but I wonder if there is a closed form expression as a function of n.
You mentioned that the area is proportional to the the square of the side length, but it could be difficult to calculate the side lengths that are involved.
Hint: The area is proportionate to the distance from the center.
Let $ \omega$ be a $n$th root of unity, and $\omega^i$ be the vertices of the polygon.
What is the distance of a side of the regular polygon from the origin?
What is the distance of a diagonal of the regular polygon from the origin?
Hence, the ratio of areas is