Both questions have exact explicit answer, which is explained in any good textbook on analytic functions. A region on the Riemann sphere is called a digon if its boundary consists of
two arcs of circles. Let $a$ and $b$ be the common endpoints of these arcs. 
Then
$$f(z)=\frac{z-a}{z-b}$$
sends $a,b$ to $0,\infty$, and the arcs to rays. So the image of our region is a sector. The interior angle at a corner of the digon be $\pi\alpha$. Then the interior angle at the vertex of the sector is also $\pi\alpha$. Next $f_1(z)=z^{1/\alpha}$ maps this sector onto a half-plane. And the final ingredient
is  conformal map of this half-plane onto the unit disk.

EDIT. Exact computation is a bit messy, but asymptotics seems to be
$\mathrm{cap}(A_r)=1+r^2+O(r^3),$ as $r\to 0$.