Going through the process of finding the derivative, which is $\dfrac{1}{2\sqrt{x+5}}$ ,and substituting x gives an undefined slope, as you end up taking the square root of a negative number
I know that the point exists somewhere across the tangent line, but I don't know how to translate this into finding an answer.
The tangent line to the point $(a,f(a))$ is given by $$y(x) = f(a)+ f'(a) (x-a) = \sqrt{a+5} + \frac{x-a}{2 \sqrt{a+5}}$$
You want to find a point $a$ whose tangent line crosses $(-8,1)$, so you need to solve $$ 1 = \sqrt{a+5} + \frac{-8-a}{2 \sqrt{a+5}} $$ whose acceptable solution is $a=4$
There is no square root problem since the tangent line is defined over all reals, even though the function you started with wasn't