Well, I decided to include some additional information.
Definition 1. Let $\mathcal{C}$ and $D$ be categories, $T\colon\mathcal{C}\to\mathcal{D}$ and $S\colon\mathcal{D}\to\mathcal{C}$ be functors. Then the pair $(T,S)$ is called an equivalence iff $S\circ T\cong I_{\mathcal{C}}$ and $T\circ S\cong I_{\mathcal{D}}$. In this case functors $T$ and $S$ are also called equivalences, and categories $\mathcal{C}$ and $\mathcal{D}$ are called equivalent.
It is a basic definition and Tim's answer shows why we need to use equivalence even more frequently than isomorphism. Here's another important definition:
Definition 2. Let $\mathcal{C}$ be a category, $\mathcal{S}$ be a subcategory of $\mathcal{C}$. Then the category $\mathcal{S}$ is called a skeleton of $\mathcal{C}$ iff it is a full subcategory of $\mathcal{C}$ and every object of $\mathcal{C}$ is isomorphic to precisely one object of $\mathcal{S}$.
Note, that if the axiom of choice holds, then every category has a skeleton. See also nLab article. The connection between equivalences of categories and their skeletons is described in the following proposition:
Proposition 1. Let $\mathcal{C}$ and $\mathcal{D}$ be categories, $\mathcal{S}_{\mathcal{C}}$ and $\mathcal{S}_{\mathcal{D}}$ be their skeletons. Then $\mathcal{C}\simeq \mathcal{D}$ iff $\mathcal{S}_{\mathcal{C}}\cong\mathcal{S}_{\mathcal{D}}$.
The proof follows from the fact that every category is equivalent to its skeleton and if two skeletal categories are equivalent, then they are isomorphic. You can also search Mac Lane's "Categories for the working mathematician" for the details.
Thus we can use the notion of skeleton instead of the original definition of equivalence, but sometimes it is not a simplification. As it was mentioned, even an attempt to prove that a category has a skeleton may lead to the set-theoretical difficulties. Tim also gave arguments.
You write: But why go through this whole process of defining this notion of equivalent categories if we can just create a single equivalence classes of objects via the equivalence relation of being isomorphic, and make morphisms defined on the same equivalence class "the same?"
Okay, it could be a good idea if we want to define something like a skeleton. But it isn't, because the straightforward applying this idea leads to wrong definition. Let's try to do this.
Definition 3. Let $\mathcal{C}$ be a category. Then define the graph $\text{Equiv}(\mathcal{C})$ in the following way: $\text{Obj}(\text{Equiv}(C))=\text{Obj}(\mathcal{C})/\cong_{\mathcal{C}}$ and $$\text{hom}_{\text{Equiv}(\mathcal{C})}([a],[b])=(\coprod_{a'\in[a],b'\in[b]}\text{hom}_{\mathcal{C}}(a',b'))/[(f\sim g)\Leftrightarrow(\exists a,b\in \text{Iso}(\mathcal{C})|\quad g\circ a=b\circ f) ].$$
But the graph $\text{Equiv}(\mathcal{C})$ doesn't inherit the composition law from $\mathcal{C}$. The graph $\text{Equiv}(\mathcal{C})$ doesn't even coincide with graph of any skeleton of $\mathcal{C}$ in general case. For example, it may paste two morphisms with the same domain: in the category $\mathbf{Finord}$ we have $\text{end}_{\text{Equiv}(\mathbf{Finord})}([2])=\text{hom}_{\text{Equiv}(\mathbf{Finord})}([2],[2])\cong2$, but $\text{end}_{\mathbf{Finord}}(2)=2^2=4$.
Best Answer
There is a simple relation between the two.
If $X$ is path-connected, then the fundamental group of $X$, expressed as a 1-element category, is a skeleton of its fundamental groupoid.
The more relevant analogy here is the preorder associated with a category, which is an example of $(-1)$-truncation. Given a category $C$, we can give the objects a pre-order by writing $a \leq b$ iff there is some morphism $a \to b$. We can then quotient the objects by equivalence to get a partial order.
Analogously, the fundamental groupoid is a higher-order truncation of the fundamental 2-groupoid. In the fundamental 2-groupoid, we also have paths between paths. But when we pass to the fundamental groupoid, we suppress the paths between between paths (or, equivalently, pretend that there is at most one path between paths). We can then quotient the paths by equivalence to get a set of paths between any two points up to homotopy equivalence.