In any regular polygon with $n\ge 4$ sides, why is any side length strictly length to any diagonal length? (A diagonal is defined as the line segment joining non-adjacent vertices)
This is intutitvely clear to me, but I am having trouble finding a formal proof. The angle between two successive sides is $(n-2)\pi/n$ and I feel that should be a starting point.

As any regular polygon can be inscribed in a circle, you can use the chord length formula, which is $$ l = 2r\sin\frac{\theta}{2} $$ where $\theta$ is the angle subtended at the center by the chord.
In your case every diagonal has larger $\theta$ than the sides and as $\sin\frac{\theta}{2}$ is increasing for $\theta\in [0,\pi]$ the result follows.