I don't believe the first claim is true, but I can give a somewhat formal argument for the connectivity of $\Delta_{\le n} \times_{\Delta} \Delta_{/m}$.
Let us write $u$ for the inclusion $\Delta_{\le n} \to \Delta$. The crucial result follows the following special case of Appendix A of https://arxiv.org/abs/2207.09256:
Theorem 1. Given a diagram $F : \Delta \to \mathcal{S}_{\le n-1}$ the canonical map $\lim_{\Delta} F \to \lim_{\Delta_{\le n}} u^*F$ is invertible.
(This may already be the result you were after, but we can carry this through to actually obtain the connectivity result you requested.)
Fix an arbitrary $F : \Delta \to \mathcal{S}_{\le n-1}$. By Theorem 1, we know that the following is an equivalence:
\begin{align*}
&\lim F
\\
&\cong \hom_{\mathbf{Fun}(\Delta,\mathcal{S})}(\mathbf{1}, F)
\\
&\to \hom_{\mathbf{Fun}(\Delta_{\le n},\mathcal{S})}(u^*\mathbf{1}, u^*F)
\\
&\cong \hom_{\mathbf{Fun}(\Delta_{\le n},\mathcal{S})}(\mathbf{1},
u^*F)
\\
&\cong \lim u^*F
\end{align*}
Transposing, we conclude that $\hom_{\mathbf{Fun}(\Delta,\mathcal{S})}(\mathbf{1}, F) \to \hom_{\mathbf{Fun}(\Delta,\mathcal{S})}(u_!u^*\mathbf{1}, F)$ is an equivalence and, consequently, that $u_!u^* \mathbf{1} \to \mathbf{1}$ is orthogonal to any $(n-1)$-truncated object in $\mathbf{Fun}(\Delta, \mathcal{S})$. Accordingly, $u_!u^*\mathbf{1} = u_!\mathbf{1}$ is $n$-connected. We therefore conclude that $(u_!\mathbf{1})(m) : \mathcal{S}$ is $n$-connected for any $m : \Delta$. Let us unfold this using the formula for left Kan extensions:
$$
(u_!\mathbf{1})(m) =
\mathrm{colim}_{
\Delta_{\le n}
\times_{\Delta}
\Delta_{/m}
} \mathbf{1}
= L(\Delta_{\le n} \times_{\Delta} \Delta_{/m})
$$
The conclusion then follows.
Incidentally, this is just slight alteration of the usual proof of one direction of Quillen's theorem A. The other direction (that suitably connective fibers implies $n$-cofinality) also holds.