In normal line integration, from what I understand, you are measuring the area underneath $f(x,y)$ along a curve in the $x\text{-}y$ plane from point $a$ to point $b$.
But what is being measured with complex line integration, when you go from a point $z_1$ to a point $z_2$ in the complex plane?
With regular line integration I can see $f(x,y)$ maps $(x,y)$ to a point on the $z$ axis directly above above/below $(x,y)$.
But in the complex case, when you map from the domain $Z$ to the image $W$, you are mapping from $\mathbb{R^2}$ to $\mathbb{R^2}$ ...it is not mapping a point to 'directly above/below'...so I don't have any intuition of what is happening with complex line integration.

Forget about areas for the moment.
Consider the following situation: At the begin you are at the origin of the $x$-axis and have to compress a spring which is attached far away to the right. Assume that when the left end of the spring is at a given $x\geq0$ then it presses back with force $f(x)$. If the force were a constant $F$ then the work $W$ done when pushing a cart from $x_0$ to $x_1$ along the $x$-axis would be $W=F\cdot(x_1-x_0)$. But in our case the force is variable. When you compress the spring by pushing a cart to the right, and after some time you are at the point $a>0$ then the total amount $W$ of work done in this process is represented by $$W\doteq \sum_{k=1}^N f(\xi_k)\ (x_k-x_{k-1})\doteq \int_0^a f(x)\ dx\ ,$$ where $0=x_0 < x_1 < \ldots < x_N=a$ is a partition of the interval $[0,a]$, and $x_{k-1}\leq\xi_k\leq x_k$ $\ (1\leq k\leq N)$.
Analogously in the complex domain for the purpose of line integrals you should not consider the given $z\mapsto f(z)$ as a mapping of the $z$-plane to some other domain, but as a "complex scalar field" which defines at each point $z\in{\rm dom}(f)$ a certain "complex force" $f(z)$. For a constant such force $F\in{\mathbb C}$ the "complex work" done when pushing a cart from $z_0$ to $z_1$ along a straight line is given by $F\cdot(z_1-z_0)\in{\mathbb C}$, where $\cdot$ denotes the ordinary product in ${\mathbb C}$.
Assume now that you are given a curve $$\gamma:\quad t\mapsto z(t)\qquad(a\leq t\leq b)\ .$$ Then the total "complex work" done when you push a cart along this curve would be represented by $$W\doteq \sum_{k=1}^N f\bigl(z(\tau_k)\bigr)\bigl(z(t_k)-z(t_{k-1})\bigr)\doteq \int_a^b f\bigl(z(t)\bigr) z'(t)\ dt =:\int_\gamma f(z)\ dz\ .$$