[guided]The cohomological index is controlled by the first Stiefel-Whitney class of the orbit double cover, so the key question is: how are the two orbit double covers related by $f$?
Let
\begin{align*}
\pi_X:X\to X/(\mathbb Z/2)
\end{align*}
and
\begin{align*}
\pi_Y:Y\to Y/(\mathbb Z/2)
\end{align*}
be the orbit projection maps. By the principal-bundle hypothesis in the theorem statement, these orbit projections are principal $\mathbb Z/2$-bundles, equivalently double covers with deck group $\mathbb Z/2$. Define
\begin{align*}
w_X:=w_1(\pi_X)\in H^1(X/(\mathbb Z/2);\mathbb Z/2)
\end{align*}
and
\begin{align*}
w_Y:=w_1(\pi_Y)\in H^1(Y/(\mathbb Z/2);\mathbb Z/2).
\end{align*}
The descended map $\bar f:X/(\mathbb Z/2)\to Y/(\mathbb Z/2)$ satisfies
\begin{align*}
\bar f\circ \pi_X=\pi_Y\circ f.
\end{align*}
This equation says that the double cover of $X/(\mathbb Z/2)$ obtained from $X$ is the pullback of the double cover of $Y/(\mathbb Z/2)$ along $\bar f$. To make the identification explicit, define
\begin{align*}
\Phi:X\to \bar f^*Y
\end{align*}
by $\Phi(x):=(\pi_X(x),f(x))$, where
\begin{align*}
\bar f^*Y=\{(b,y)\in X/(\mathbb Z/2)\times Y: \bar f(b)=\pi_Y(y)\}.
\end{align*}
The equality $\bar f(\pi_X(x))=\pi_Y(f(x))$ verifies that $\Phi(x)$ belongs to the pullback space. Why is this an isomorphism on fibers? Fix $x\in X$. Since the action on $X$ is free, the fiber of $\pi_X$ over $\pi_X(x)$ consists exactly of $x$ and $\tau_X(x)$. Since $f$ is equivariant, these two points are sent to $f(x)$ and $\tau_Y(f(x))$. Since the action on $Y$ is free, those are exactly the two points in the fiber of $\pi_Y$ over $\pi_Y(f(x))$. Thus $\Phi$ is a fiberwise bijective equivariant bundle map. This is enough to identify the two double covers, but we spell out the topological point. On any open set $V\subset X/(\mathbb Z/2)$ over which both principal $\mathbb Z/2$-bundles are trivial, the two bundles are written as $V\times \mathbb Z/2$. In these coordinates an equivariant map over $V$ must be $(b,\epsilon)\mapsto (b,\epsilon_0(b)\epsilon)$ for a function $\epsilon_0:V\to \mathbb Z/2$. Because $\mathbb Z/2$ is discrete and the map is continuous, this formula has the continuous inverse $(b,\epsilon)\mapsto (b,\epsilon_0(b)^{-1}\epsilon)$. The local inverses agree with the same global formula on overlaps, so $\Phi$ is an isomorphism of double covers and identifies $\pi_X$ with $\bar f^*\pi_Y$.
Therefore naturality of the first Stiefel-Whitney class for pullback double covers applies to the map $\bar f:X/(\mathbb Z/2)\to Y/(\mathbb Z/2)$ and the double cover $\pi_Y:Y\to Y/(\mathbb Z/2)$. It gives
\begin{align*}
w_1(\pi_X)=\bar f^*w_1(\pi_Y).
\end{align*}
With the abbreviations $w_X=w_1(\pi_X)$ and $w_Y=w_1(\pi_Y)$, this becomes
\begin{align*}
w_X=\bar f^*w_Y.
\end{align*}
Now we pass from classes to powers. The induced map on cohomology
\begin{align*}
\bar f^*:H^*(Y/(\mathbb Z/2);\mathbb Z/2)\to H^*(X/(\mathbb Z/2);\mathbb Z/2)
\end{align*}
is a graded ring homomorphism, so it preserves cup products. Hence, for every integer $k\geq 0$,
\begin{align*}
w_X^k=(\bar f^*w_Y)^k=\bar f^*(w_Y^k).
\end{align*}
This identity is the monotonicity mechanism: every power of the Stiefel-Whitney class on $X$ is pulled back from the corresponding power on $Y$.[/guided]