I've tried a bunch of different approaches to this question (and would particularly appreciate some hints that don't give the whole thing away immediately).
I've noticed that if $S$ contains some finite subsets, then for each $n \in \mathbb{N}$ there is at most one subset of size $n$ in the collection $S$ as $S$ can't contain duplicates (in order to satisfy the given condition). Certainly if $A_i$ is a finite subset contained in $S$ of size $i$, then $A_i \subset A_j$ if $i > j$.
I've tried considering the possibilities where there are some finite subsets in the collection $S$, and then we can also add in infinite-size subsets that are each a superset of all of the finite subsets. However it seems rather difficult to visualise what happens when you consider infinite subsets of $\mathbb{N}$ that can't be obtained by removing finitely many elements from $\mathbb{N}$. What are good approaches to take to figure out whether such a set can be uncountable - is there an element of construction here?