Let $\Sigma_{g,n}$ denote a compact orientable genus $g$ surface with $n$ boundary components. Assume that $g \geq 1$ and fix a basepoint $p \in \Sigma_{g,n}$. Define $S \subset [\pi_1(\Sigma_{g,n},p),\pi_1(\Sigma_{g,n},p)]$ to be the set of all elements of $\pi_1(\Sigma_{g,n},p)$ that can be realized by simple closed $p$-based curves $\gamma$ that separate $\Sigma_{g,n}$ into two components, one of which is homeomorphic to a one-holed torus with boundary component $\gamma$. It is not hard to show that if $p$ is in the interior of $\Sigma_{g,n}$, then $S$ generates $[\pi_1(\Sigma_{g,n},p),\pi_1(\Sigma_{g,n},p)]$. For instance, this is Lemma A.1 in my paper "Cutting and Pasting in the Torelli Group", though I'm sure that many other people have observed this over the years.

Assume now that $p$ lies on one of the boundary components of $\Sigma_{g,n}$. Question : Does $S$ still generate $[\pi_1(\Sigma_{g,n},p),\pi_1(\Sigma_{g,n},p)]$?

The thing that makes this difficult is the following. If $\gamma \in \pi_1(\Sigma_{g,n},p)$ can be realized by a simple closed curve and $p$ is in the interior of the surface, then all conjugates of $\gamma$ can also be realized by simple closed curves. However, this is false if $p$ is on the boundary.

I suspect that the answer is no, so here is a more general question. Continue to assume that $p$ lies on one of the boundary components of $\Sigma_{g,n}$. The group $\text{Diff}(\Sigma_{g,n},p)$ acts on $\pi_1(\Sigma_{g,n},p)$, and $S$ consists of a single orbit under this action. Question : does there exist a finite subset $T$ of $[\pi_1(\Sigma_{g,n},p),\pi_1(\Sigma_{g,n},p)]$ such that the $\text{Diff}(\Sigma_{g,n},p)$-orbit of $T$ generates $[\pi_1(\Sigma_{g,n},p),\pi_1(\Sigma_{g,n},p)]$?

Funny things might happen in the low-genus cases, so I should mention that I'm most interested in the case where $n=1$ and $g$ is large.