Everything on this question is in complex plane.
As the book describes a property of a winding number, it says that:
Outside of the [line segment from $a$ to $b$] the function $(z-a) / (z-b)$ is never real and $\leq 0$.
Here, the above statement should be interpreted as "never (real and $\leq 0$)".
If anyone could explain why this is true that would be great. I do get why any point on the line segment (other than $b$, in which case the denominator is $0$) has to satisfy the condition that $(z-a) / (z-b)$ is real and $\leq 0$, but I am not sure how to prove why any point not on the line has to satisfy the condition also.
Here, $a$ and $b$ are arbitrary complex number in a region determined by a closed curve in the complex plane; both points lie on the same region.
Sorry, I misread the question at first; thanks to Eric for pointing it out. Also see his answer for the geometric perspective.
Anyways, if the statement were true, then there exists $c$ such that $k(c - b) = c - a$ for a real number $k \le 0$. That is, $$a - kb = (1 - k)c\\ \text{Let } l = (1 - k)^{-1}, \text{where } 0 \lt l \le 1.\\ c = {a - kb\over 1 - k} = la + (1 - l)b = a + (1 - l)(-a + b)$$
Yet, $c$ cannot intersect the line segment from $a$ to $b$. That is, $c \neq a + m(b - a)$ for any real number $0 \le m \le 1$. But we have just found $0 \le 1 - l \lt 1$ above. So the statement can only be false.
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Original answer:
I'm not sure if that statement as displayed is actually true. Say f{z} = (z - a)/(z - b), and let a = -1 - i, b = 1 + i. f{c} = 3 for c = 2 + 2i.