Incomplete proof (that the conjecture is true).
Let $\sigma$ be some target permutation, and we seek $p(\sigma) = P(\sigma_i \circ \sigma_j = \sigma)$. The event is equivalent to $\sigma_i^{-1} \circ \sigma = \sigma_j$. So the question becomes two-part:
Is $\sigma_i^{-1} \circ \sigma$ a derangement?
Conditioned on $\sigma_i^{-1} \circ \sigma$ being a derangement, what is the probability that $\sigma_j$ equals that derangement? The answer to the 2nd question is simply $1/|D_n|$. I.e.
$$p(\sigma) = P(\sigma_i^{-1} \circ \sigma \in D_n) \times \frac1{|D_n|}$$
This explains why the identity $\sigma^*$ is favored: $P(\sigma_i^{-1} \circ \sigma^* \in D_n) = 1$. It has in fact the maximum $p(\sigma)$ among all target $\sigma$'s.
Now, $\sigma_1^{-1}$ is just a random derangement, so the question becomes calculating, for any given target $\sigma$, the probability $f(\sigma) = P(\pi \circ \sigma \in D_n)$ where $\pi$ is a random derangement, and we will have $p(\sigma) = f(\sigma) / |D_n|$.
The rest of this answer is non-rigorous. I would imagine the main thing (the only thing?) that matters is the number of fixed points of $\sigma$. The more fixed points, the higher $f(\sigma)$, because:
Any fixed point of $\sigma$, e.g. $\sigma(i) = i$, will certainly not be fixed any more in $\pi \circ \sigma$, i.e. $\pi(\sigma(i)) \neq \sigma(i) = i$.
However, any non-fixed point of $\sigma$, e.g. $\sigma(i) = j \neq i$, might unluckily become fixed in $\pi \circ \sigma$, i.e. $\pi(\sigma(i)) = i$, if $\pi$ happens to "undo" $\sigma$ at that point, i.e. $\pi(j) = i$.
And of course if $\pi \circ \sigma$ has a fixed point then it is $\notin D_n$. I.e. every non-fixed point of $\sigma$ is a sort of "potential reason" to violate $\pi \circ \sigma \in D_n$, thereby lowering $f(\sigma)$.
Anyway, based on this non-rigorous argument, the lowest $f(\sigma)$ would happen if $\sigma$ has no fixed points, i.e. it is itself a derangement. Without loss, any derangement would do for $\sigma$ in this case, and $f(\sigma)$ becomes the probability that two derangements compose to make a third derangement -- which is exactly addressed in this answer. According to it, the asymptotic value of the probability is $1/e$.
I.e., if you believe that answer (it's too advanced for me to check), and if you believe me that $\sigma$ being itself a derangement is the "worst case", then your conjecture is true, with bounds $c = 1/e^2, C = 1/e$.
Incidentally, I tried using the union bound, but as expected it is not strong enough. Let $k$ denote the number of non-fixed points of $\sigma$ (i.e. $n-k = $ no. of fixed points of $\sigma$), and let $\sigma(i) = j \neq i$ denote a typical such non-fixed point. We have:
$$\pi \circ \sigma \in D_n \iff \bigcap \pi(j) \neq i$$
$$P(\pi \circ \sigma \in D_n) = 1 - P(\bigcup \pi(j) = i) \ge 1 - k P(\pi(j) = i) = 1 - {k \over n-1}$$
where the intersection and union are both over all the non-fixed points of $\sigma$, and $P(\pi(j) = i) = 1/(n-1)$ by symmetry. However, this bound not only fails for $k=n$ (i.e. the "hard" case of $\sigma$ being a derangement), it also does not give an asymptotic bound away from $0$ for e.g. $k = n-10$.