Computing the Density for One Disk
Without loss of generalization, let the radius of the larger circle be $1$ and the radius of the smaller circle be $s$.
The probability of a point at a distance $r$ from the center of the circle of radius $1$ being in a circle of radius $s$, whose center is uniformly distributed in a circle of radius $1-s$ concentric with the circle of radius $1$, is the ratio of the area of the intersection of a circle of radius $1-s$ with a circle of radius $s$ whose centers are at a distance $r$ divided by the area of the circle of radius $1-s$.

Using the Law of Cosines and Heron's formula, we get
$$
\rho(s,r)=\left\{\begin{array}{}
1&\text{if }r\le2s-1\\[12pt]
\frac{s^2}{(1-s)^2}&\text{if }r\le1-2s\\
\frac{s^2\cos^{-1}\left(\frac{r^2+2s-1}{2rs}\right)+(1-s)^2\cos^{-1}\left(\frac{r^2-2s+1}{2r(1-s)}\right)-\frac12\sqrt{\left(1-r^2\right)\left(r^2-(2s-1)^2\right)}}{\pi(1-s)^2}&\text{if }r\gt|1-2s|
\end{array}\right.
$$
Computing the Density for Multiple Disks
Each of the disks is independent of the others, so the density for the intersection of $n$ disks is $\rho(s,r)^n$. Thus, the expected overlap of all $n$ disks is
$$
2\int_0^1\rho(s,r)^n\,r\,\mathrm{d}r
$$
If $0\le r\le2s-1$, then $\rho(s,r)=1$; otherwise, $\rho(s,r)\lt1$. Therefore,
$$
\begin{align}
\lim_{n\to\infty}2\int_0^1\rho(s,r)^n\,r\,\mathrm{d}r
&=2\int_0^{2s-1}r\,\mathrm{d}r\\
&=(2s-1)^2
\end{align}
$$
Since $s=\sqrt{\frac\omega\Omega}$, this verifies the formula guessed when $\frac\omega\Omega\ge\frac14$. When $\frac\omega\Omega\lt\frac14$, the limit of the expected values is $0$.
Explanation of the Claim in the Second Paragraph
Symmetry says that the density will be radially symmetric, so we will evaluate at the point $(r,0)$.
Consider
$$
\frac1{\pi(1-s)^2}\iint\overbrace{[|t|\lt1-s]}^{t\in B(1-s,0)}\,\overbrace{[|x-t|\lt s]}^{x\in B(s,t)}\,\mathrm{d}t\,\delta(x-(r,0))\,\mathrm{d}x
$$
Integrating in $t$ first, we get the average of a disk of radius $s$ whose center has been placed uniformly in the disk of radius $1-s$ centered at the origin. Integrating in $x$, against the delta function, we get evaluation of the resultant average at the point $(r,0)$. This gives the average inclusion probability at $(r,0)$.
The substitution $t\mapsto x-t$ yields
$$
\frac1{\pi(1-s)^2}\iint[|x-t|\lt1-s]\,[|t|\lt s]\,\mathrm{d}t\,\delta(x-(r,0))\,\mathrm{d}x
$$
and now we can apply Fubini to change the order of integration
$$
\frac1{\pi(1-s)^2}\iint[|x-t|\lt1-s]\,\delta(x-(r,0))\,\mathrm{d}x\,[|t|\lt s]\,\mathrm{d}t
$$
Integrating in $x$ yields
$$
\frac1{\pi(1-s)^2}\int[|(r,0)-t|\lt1-s]\,[|t|\lt s]\,\mathrm{d}t
$$
which is the area of the intersection of a disk of radius $s$ and a disk of radius $1-s$ whose centers are separated by a distance $r$ divided by area of a disk of radius $1-s$.