On Wikipedia, the gluing and locality properties of a Sheaf are defined in terms of elements $s$ of the object $S$ associated with $\mathscr{F}(U)$.
I have two points of confusion.
I thought objects in a category don't necessarily have elements so does this definition even makes sense for categories outside of sets with structure?
My second question is, assuming $S$ is a set. What is even met by the gluing compatibility conditions,
$$res_{V \cap W }(s_i) = res_{V \cap W }(s_j) $$
For instance in the case of the skyscraper sheaf at a point $p$, give an open covering of $U$, $s_i$ may only even exist for the $U_i$ containing $p$.
From the definitions, it feels like you need to elements of a set to make the definition to make things work and implicitly a function associated with each element defined for every open subset of $U$ that maps to the empty set over subsets where an element disappears.
My thinking must be horribly wrong here but I'm hoping someone can clarify these misconceptions.
A (pre)sheaf on a category $\mathcal{C}$ is a functor from $\mathcal{C}^{\rm op} \to \mathsf{Set}$ or sets with extra structure: Abelian groups, rings, modules, etc. $\mathcal{C}$ is often the category of open sets on a topological space. In particular, $\mathscr{F}(U)$ is always a set, by definition.
In the equation $\operatorname{res}_{V \cap W }(s_i) = \operatorname{res}_{V \cap W }(s_j)$ we assume that $s_i \in \mathscr{F}(V)$ and $s_j \in \mathscr{F}(W)$. Or to use the notation on Wikipedia: $s_i \in \mathscr{F}(U_i)$ and $s_j \in \mathscr{F}(U_j)$ with $$ \operatorname{res}_{U_i \cap U_j}(s_i) = \operatorname{res}_{U_i \cap U_j}(s_j) $$ For a skyscraper sheaf (of sets, let's say) $\mathscr{F}(U) = \{0\}$ (the terminal object of $\mathsf{Set}$ up to isomorphism) for all $U$ not containing $p$ and hence $s_i = 0$ for all $U_i$ not containing $p$. These $s_i$ still exist.
Maybe it would be best for you to read some examples of sheaves and think through the glueing axiom. For example, the sheaf of continuous functions on a topological space or sheaves of smooth/continuously differentiable functions on a manifold.