Information:
a-) $X$ and $Y$ are two continuous random variables on $\mathbb{R}$ having continuous distribution functions $F$ and $G$ with $G(y)\geq F(y)$ for all $y$.
b-) $S^X_n=\sum_{i=1}^n X_i$, $S^Y_n=\sum_{i=1}^n Y_i$, $A>0$, and $B<0$; where $X_i$ and $Y_i$ are i.i.d. replicas of $X$ and $Y$ respectively.
c-) $E[X]<0$ and $E[Y]<0$.
What I know:
By coupling (since $G\geq F$), I know that there exist a pair of random variables $(X^{'},Y^{'})$ such that $X=X^{'}$ in distribution, $Y=Y^{'}$ in distribution, and $X^{'}\geq Y^{'}$ almost surely. Using this result, I also have $S_n^{X^{'}}=\sum_{i=1}^n X^{'}_i\geq \sum_{i=1}^n Y^{'}_i=S_n^{Y^{'}}$. Since this holds for all $n$, I am able to compare the following:
$$\tau_A^{X^{'}}=\inf\{n\geq 0:S_n^{X^{'}}\geq A\}$$ $$\tau_A^{Y^{'}}=\inf\{n\geq 0:S_n^{Y^{'}}\geq A\}$$ $$\tau_B^{X^{'}}=\inf\{n\geq 0:S_n^{X^{'}}\leq B\}$$ $$\tau_B^{Y^{'}}=\inf\{n\geq 0:S_n^{Y^{'}}\leq B\}$$
with $\tau_A^{X^{'}}\leq \tau_A^{Y^{'}}$ since $S_n^{X^{'}}\geq A$ implies $S_n^{Y^{'}}\geq A$ and similarly $\tau_B^{X^{'}}\geq \tau_B^{Y^{'}}$. Please see (for details).
Claim-$1$:
$$E[\min\{\tau_A^{X^{'}},\tau_B^{X^{'}}\}]\geq E[\min\{\tau_A^{Y^{'}},\tau_B^{Y^{'}}\}]$$
holds for any $(A,B)$ and $(X,Y)$.
Claim-$2$:
$$E[\min\{\tau_A^{X^{'}},\tau_B^{X^{'}}\}]\geq E[\min\{\tau_A^{Y^{'}},\tau_B^{Y^{'}}\}]$$
holds for any $(A,B)$ and $(X,Y)$, if additionally $\partial F/\partial G$ is increasing.