Since the map $\pi:X\to X/\sim$ is open, it's clear that the map $g:X^2\to (X/\sim)^2$ given by $g(x,y)=(\pi(x),\pi(y))$ is open. What we claim is that $g(X^2-\sim)=(X/\sim)^2-\Delta_{X/\sim}$. Indeed, if $x\nsim y$ then $\pi(x)\ne\pi(y)$ which tells us that $g\left(X^2-\sim\right)\subseteq (X/\sim)^2-\Delta_{X/\sim}$. That said, if $(\pi(x),\pi(y))\notin\Delta_{X/\sim}$ then $\pi(x)\ne \pi(y)$ so that $x\nsim y$ so that $(x,y)\in X^2-\sim$ and clearly $g(x,y)=(\pi(x),\pi(y))$. Thus, $g(X^2-\sim)=(X/\sim)^2-\Delta_{X/\sim}$ as claimed. But, since $X^2-\sim$ is open by assumption, and $g$ is an open map we have that $(X/\sim)^2-\Delta_{X/\sim}$ is open, and so $\Delta_{X/\sim}$ is closed. This gives us $T_2$ness.
$\def\RR{\mathbb{R}}$There is no separation condition which will do the job. That's a vague statement, so here is a precise one: There is a subset of $\mathbb{R}^2$ which (equipped with the subspace topology) does not have condition $\dagger$.
Proof: Let $A$ and $B$ be two disjoint dense subsets of $\mathbb{R}$, neither of which contains $0$. (For example, $\mathbb{Q} +\sqrt{2}$ and $\mathbb{Q}+\sqrt{3}$.) Let
$$X = (A \times \RR_{\geq 0}) \cup (B \times \RR_{\leq 0}) \cup (\{0\} \times \RR_{\neq 0}) \subset \RR^2.$$
Define $(x_1,y_1)$ and $(x_2, y_2)$ to be equivalent if $x_1=x_2$ and, in the case that $x_1=x_2=0$, that $y_1$ and $y_2$ have the same sign.
Verification that this is a closed equivalence relation: $X^2$ is a metric space, so we can check closure on sequence. Let suppose we have a sequence $(x_n, y_n) \sim (x'_n, y'_n)$ with $\lim_{n \to \infty} x_n=x$, $\lim_{n \to \infty} y_n=y$, $\lim_{n \to \infty} x'_n=x'$ and $\lim_{n \to \infty} y'_n=y'$. We must verify that $(x,y) \sim (x',y')$. First of all, we have $x_n = x'_n$, so $x=x'$ and, if $x=x' \neq 0$, we are done. If $x=x'=0$, we must verify that $y$ and $y'$ have the same sign. But $y_n$ and $y'_n$ weakly have the same sign for all $n$, so they can't approach limits with different signs.
Verification that $X/{\sim}$ is not Hausdorff: We claim that no pairs of open sets in $X/{\sim}$ separates the images of $(0,1)$ and $(0,-1)$. Suppose such open sets exist, and let $U$ and $V$ be their preimages in $X$. Then there is some $\delta$ such that $(A \cap (-\delta, \delta) )\times \RR_{\geq 0} \subset U$ and $(B \cap (-\delta, \delta) )\times \RR_{\geq 0} \subset B$. Then $U \cap \RR \times \{ 0 \}$ is an open set which contains $(-\delta, \delta)$. By the density of $B$, there must be a point of $B \cap (- \delta, \delta)$ in $U \cap \RR$, and then this gives an intersection between $U$ and $V$.
Best Answer
I would go about it this way (letting $Y$ represent the quotient space $X/\sim$):