I am trying to understand the concept of the winding number of a curve.
As the title suggests, I would like to figure out the winding number of C around points in the regions 1, 2, 3 and 4 (It will be the best if I can do this simply by inspection with no computations).
I denote the first loop curve $C_{1}$ then $C_{2}$ and $C_{3}$ respectively. By definition, the winding number of the curve, $C$ around $a$ is defined by: $$n(C,a)=\frac{1}{2\pi i}\int_{C} \frac{1}{z-a}dz.$$ However, I did not find the formula useful. Rather, based on https://en.wikipedia.org/wiki/Winding_number, my findings are presented below.
My answer is as follows:
Region 1: $n(C,a)=-1$.
Reason: Suppose a point, $z$ is in region 1 (being enclosed by loop 1). Since the curve is clockwise, by visual inspection, we have $n(C,a)=-1$.
Region 3: $n(C,a)=-1$.
Reason: Same explanation as above.
Region 2: $n(C,a)=1$.
Reason: This time, the loop is anti-clockwise.
Region 4: This is slightly tricky and I am unsure.
Can someone help me to verify if my winding number for regions 1, 2 and 3 are correct and is my way of determining winding number correct?

You are right about regions $1$, $2$, and $3$.
About region $4$: from each $p$ in that region you can draw a ray starting at $p$ and going to $\infty$ which doesn't even touch the line. Therefore, yes, the answer is $0$.