(I am most interested in the case $X=\mathbb R^2$, but of course one could ask the same question for manifolds, or metric spaces in general.)
Let $\text{Com}(\mathbb R^2)$ denote the space of nonempty compact subsets of the plane, equipped with the Hausdorff metric. Let $S_\bullet:[0,1]\to\text{Com}(\mathbb R^2)$ be a continuous path, and let $p\in S_0$. Must there exist a path $\gamma:[0,1]\to\mathbb R^2$ such that $\gamma(0)=p$, and $\gamma(t)\in S_t$ for all $t\in[0,1]$?