If we take the brutal step of resorting to trigonometry and calculus we can prove the statement using general techniques. It may seem long and technical- but I think it demonstrates re-usable methods that give some intuition (after you use them a few times!).
To prove: the regular n-gon has the maximal area of any n-gon inscribed inside the unit circle.
Proof sketch:
We will prove only the lemma that if theta1, and theta2 are angles summing to C < pi then sum of the areas of the area of the figure formed by the convex hull of (0,0), (sin(theta1),cos(theta1)), (0,1), and (-sin(theta2),cos(theta2)) is maximized for a given C when theta1=theta2. That is: the area formed by subdividing a segment of the circle of angle theta1+theta2 is maximized by dividing in the middle. This would let us prove the theorem as it implies any non-regular division can be improved by re-centering one of the sub-divisions.
Proof of lemma:
The area of triangle formed by the convex hull of the center of a unit circle and the points (sin(theta/2),cos(theta/2)), (-sin(theta/2),cos(theta/2)) is (1/2) base height = (1/2) (2 sin(theta/2)) cos(theta/2) = sin(theta/2) cos(theta/2).
So if f(theta1,theta2) is the area of the two inscribed triangles of angles theta1 and theta2 we have: f(theta1,theta2) = sin(theta1/2) cos(theta1/2) + sin(theta2/2) cos(theta2/2)
If we add the constraint theta1+theta2=C then we expect the maximum to occur at one of theta1=0,theta2=C; theta1=C,theta2=0 or an point where the Lagrange auxiliary function L(theta1,theta2,lambda) = f(theta1,theta2) + lamba (theta1+theta2-C) has a zero gradient (gradient with respect to theta1, theta2))
Gradient((theta1,theta2),L) = (1/2) (cos(theta1/2)^2 -sin(theta1/2)^2, cos(theta2/2)^2 -sin(theta2/2)^2) + lambda (1,1)
For this vector quantity to be equal to zero we would have to have the coordinates equal (so the lambda (1,1) can stomp them out): cos(theta1/2)^2 -sin(theta1/2)^2 = cos(theta2/2)^2 - sin(theta2/2)^2
But cos(x)^2 -sin(x)^2 = 1 - 2 sin(x)^2 which is a 1 to 1 function in the range [0,pi) so to have cos(theta1/2)^2 -sin(theta1/2)^2 = cos(theta2/2)^2 -sin(theta2/2)^2 we must have theta1=theta2.
So we check that f(C/2,C/2) >= max(f(C,0),f(0,C)) and we are done.
Again I know that is long and technical (and bringing in overly big hammers)- but the steps are all standard re-usable ideas. (actually longer than I even intended)