$\newcommand\S{\mathscr S}$Let $\S$ be a collection of nonempty subsets of a finite set $S$ such that $A\not\subset B$ for any distinct $A$ and $B$ in $\S$.
Does then there always exist a function $f\colon S\to(0,\infty)$ such that $\sum_{s\in A}f(s)=1$ for all $A\in\S$?
The answer to this question is yes if each set $A$ in $\S$ is of cardinality $\le2$.
\S
work for you but not for me?) $\endgroup$