I believe the answer is yes. The argument is a little bizarre (using contradiction in what feels, for now, like an essential way). I feel there should be a cleaner version, but this is what I have for now. By the way, I have replaced your $\pi_{Y=y}(\cdot)$ with the notation $\mathbb P(\cdot|Y=y)$ which feels a bit more familiar to me.
Let $V_Y(x)=\mathbb E(\tanh^2 Y|X=x)-\mathbb E(\tanh Y|X=x)^2$, that is the variance of $\tanh Y$ conditioned on $X=x$. Similarly, let $V_X(y)$ be the variance of $\tanh X$ conditioned on $Y=y$. The function $V_Y(x)$ is $\mu$-a.e. zero if and only if $Y$ is measurable with respect to $X$; and likewise $V_X(y)$ is $\nu$-a.e. zero if and only if $X$ is measurable with respect to $Y$. (The role of the hyperbolic tangent is to ensure that these quantities are finite).
We now prove your claim by contradiction. Suppose your conditions hold, but that $X$ is not measurable with respect to $Y$. Then $V_X$ is not $\nu$-a.e. zero. It follows that there exists $\delta>0$ and a set $B$ with $\nu(B)>0$ with the property that $V_X(y)>\delta^2$ for all $y\in B$.
We now apply your second condition: let $A=\{x\colon \mathbb P(Y\in B|X=x)=1\}$. By your condition, $\mu(A)>0$. Using countable additivity, let $A_1$ be a subset of $A$ with $\mu(A_1)>0$ of the form $A_1=\{x\in A\colon \tanh x\in (c,c+\delta)\}$.
Finally, let $B_1=\{y\colon \mathbb P(X\in A_1|Y=y)=1\}$. By the first condition, $\nu(B_1)>0$. We claim that $B_1\subset B$ up to a set of measure 0. To see this, notice that $\{Y\in B_1\}$ is a subset of $\{X\in A_1\}$ (up to a set of measure 0); and $\{X\in A_1\}$ is a subset of $\{X\in A\}$, which is a subset (up to measure 0) of $\{Y\in B\}$.
If $y\in B_1$, then $V_X(y)<\frac{\delta^2}4$ since conditioned on $Y=y$, $\tanh X\in (c,c+\delta)$. However since $y\in B$, we also have $V_X(y)>\delta^2$. This is a contradiction.