I have a very hard time accepting the differential-geometric definition of a vector as a derivative operator, $$v = v^{\mu} \partial_{\mu}.$$ I want to make sure that the following line of reasoning is correct - if it is, then I will finally be at peace with the aforementioned definition.
(Geometrical) vectors are most naturally introduced as displacements in an affine space $\mathbb{A}$. E.g. a geometrical vector $\vec{v} \in \mathbb{V}$ (a vector space) can be thought of as a difference of two points (positions) $\mathcal{P, Q} \in \mathbb{A}$, so that $$\vec{v} = \mathcal{Q}-\mathcal{P}.$$ We can think of $\vec{v}$ as a good old fashioned arrow starting at $\mathcal{P}$ and ending at $\mathcal{Q}$. Of course, we cannot play this game outside of $\mathbb{A}$, but this is still valid locally in any manifold $\mathcal{M}$ since manifolds are locally Euclid (more specific, affine) spaces. If $\gamma:\mathbb{R} \to \mathcal{M}$ is a curve in $\mathcal{M}$ with $\gamma(0) = \mathcal{P}$, we can subtract $\mathcal{P}$ from its infinitesimally close neighbor, which lies on $\gamma$, to get a tangent vector$$\vec{v} = \gamma'(0).$$
First question: Am I correct to assume that $\gamma'(0)$ can be thought of as an arrow lying in the tangent space $T_{\mathcal{P}}\mathcal{M}$, not necessarily ending anywhere in $\mathcal{M}$? Furthermore, it should be obvious from the definition that this is a pure geometrical object and not a (differential) operator?
Second question: Is the operator-vector $v = v^{\mu} \partial_\mu$ just an object isomorphic to $\vec{v}$ and is therefore also known as the tangent vector, but whose character is more algebraic and less geometric? In other words, although $\vec{v}$ (an arrow) and $v$ (a derivative) are isomorphic, they are clearly different objects?
Third question: If the answer to the last question is yes, given some coordinates $\{x^\mu\}$, we should be able to write $$\vec{v} = v^{\mu} \vec{e}_\mu,$$ where now $\vec{e}_\mu$ is a geometric vector (arrow) basis and not a differential operator $\partial_\mu$. How is $\vec{e}_\mu$ related to $\gamma$?
You're certainly on the right track. Yes, $\vec v$ is a vector in the tangent space $T_PM$, almost never a vector joining $P\in M$ to a point $Q\in M$.
The main philosophy is to think of tangent directions $\vec v$ as equivalent to directional derivatives $D_{\vec v}$. Knowing $D_{\vec v}f(P)$ for all smooth functions $f$ (defined on a neighborhood of $P$, say) tells you what $\vec v$ must be. Given a coordinate system $x^\mu$ and a representation $\vec v = \sum v^\mu \vec e_\mu$, you can think of $\vec e_\mu$ as the tangent vectors to the $x^\mu$-coordinate curves (just like we think of $\vec e_j$ in Euclidean space as the tangent vectors to the $x_j$-axis).
EDIT: In particular, note that $D_{\vec v} f(P) = df_P(\vec v) =\left(\sum v^\mu\vec e_\mu\right)(f)$, or, if you insist, $=\left(\sum v^\mu\partial_\mu\right)(f)$.