This is going to be a bit of a long post, so fair warning.
So from what I could gather from some research, on the first link below, it goes that the category $Set$ is not isomorphic to its opposite, $Set^{op}$. My issues concern proving why.
One of the answers seems to make use of properties regarding the empty set. Namely, that, for all objects $X \in Set$, the arrow $X \rightarrow \emptyset$ exists if and only if $X = \emptyset$. This arrow would be isomorphic, clearly. There also exists an arrow $\emptyset \rightarrow X$ for all objects $X \in Set$.
So in $Set^{op}$, the dual idea reverses these arrows, i.e. for all $X$ we have an arrow $X \rightarrow \emptyset$. Apparently from what I could find at the second link below, this isn't an inherent violation ... for some technical reasons that I don't really understand. But I guess I'm basically mean to take the "reversing all arrows" part of the definition of opposite category very literally, and that it doesn't inherently break any rules by itself.
So my question is, then, how exactly do these become relevant to proving $Set$ is not isomorphic to its opposite? Because if we don't really have these violations, it seems trivial to define a functor $T$ such that
- Object function: $X \mapsto T(X)$ as according to the below
- Arrow function: $(f : A \rightarrow B) \mapsto (T(f) : T(A) \rightarrow T(B))$, where $T(A) = B$ and $T(B) = A$.
But obviously that's not right since it doesn't really invoke any assumptions about $Set$ and could be generalized to prove $\mathscr{C} \cong \mathscr{C}^{op}$ for any category $\mathscr{C}$.
Supposedly, according to a third post, this has something to do with the notion of "categorical properties." Namely, that - whatever these properties are, that term hasn't come up in my course at all - these are preserved by functors - which wasn't even mentioned when we covered functors.
So I'm trying to rationalize my way through this, but I can't be sure because ... well, I can't really figure out what a categorical property is, and how that applies in this case.
Does anyone have any nudges in the right direction for me?
Link 1 - Why is every category not isomorphic to its opposite?
Link 2 - What is the opposite category of $Set$?
Link 3 - Proof that $ \textbf{Set}\ $ is not isomorphic to its dual
Let me flesh out Andreas Blass's answer at one of the questions you linked to which you seem to be misunderstanding.
What this is saying is that in $Set$ there exists an object $A$ (namely $\emptyset$) with the property that for every object $B$ and every morphism $f:B\to A$, $f$ is an isomorphism. The claim is that this is a categorical property (preserved by isomorphisms of categories*): if a category $\mathcal{C}$ has such an object $A$ and $F:\mathcal{C}\to\mathcal{D}$ is an isomorphism of categories, then $\mathcal{D}$ also has such an object.
The proof is pretty trivial: just observe that $F(A)$ will have the same property in $\mathcal{D}$. Indeed, suppose $B$ is an object of $\mathcal{D}$ and $f:B\to F(A)$ is a morphism. Then $F^{-1}(f):F^{-1}(B)\to A$ is a morphism, so by the assumed property of $A$ it is an isomorphism. Thus $f=F(F^{-1}(f))$ is also an isomorphism, as desired.
What's going on here is that we can freely "translate" between $\mathcal{C}$ and $\mathcal{D}$ by applying $F$ and its inverse, so any reasonable property of an object $A$ in $\mathcal{C}$ will also be true of the object $F(A)$ in $\mathcal{D}$.
OK, now let's get back to our story of $Set$. In the category $Set$, there is an object $A$ with the property stated above (namely $A=\emptyset$). If $Set$ and $Set^{op}$ were isomorphic, then there would exist some object $A'$ with the same property in $Set^{op}$. Let's unravel what this means. We have an object $A'$ of $Set^{op}$ (i.e., a set) such that for any object $B$ of $Set^{op}$ (i.e., a set) and any morphism $f:B\to A'$ (i.e., a function $f:A'\to B$), $f$ is an isomorphism (i.e., $f$ is a bijection). Translating this back into ordinary statements about sets as indicated in parentheses, we have a set $A'$ such that for any set $B$, every function $f:A'\to B$ is a bijection. However, no such set exists: for instance, if $A'$ is any set and $x$ is not an element of $A'$, then $B=A'\cup\{x\}$ is a set and the inclusion map $f:A'\to B$ is not a bijection.
So, no such object $A'$ of $Set^{op}$ exists, and so $Set^{op}$ is not isomorphic to $Set$.
*Actually, usually when people talk about "categorical properties", they really mean properties that are preserved by equivalences of categories, not just isomorphisms. That is a more subtle story that I won't get into here, since your question is just about isomorphisms.