I was thinking that I should separate the term $(-14i)^{0.5}$
into $(-14)^{0.5}$ and $i^{0.5}$
then into $i$ and $14^{0.5}$ and $i^{0.5}$
But Wolframalpha says that the answer is $(1-i)7^{0.5}$, and I don't think that's the same as $i^{1.5}14^{0.5}$.
How do I simplify $(-14i)^{0.5}?$
You're assuming that exponent laws like $(ab)^c = a^cb^c$ hold when dealing with complex bases and non-integer exponents. They don't. They hold as long as the bases are positive, real numbers. And they hold as long as the exponents are integers. But you need to fulfill at least one of those requirements for the laws to apply.
Also, I would be extremely catious in general when applying fractional exponents or roots to complex numbers. It is difficult to do correctly (it can be tricky to even define what "correctly" means).
Hopefully, you stop writing things like $(-14i)^{0.5}$, and then you don't need to worry about how to calculate them any more. But if that's not an option for you, it often helps to think geometrically. Where in the complex plane is $-14i$? What geometric operation does $^{0.5}$ correspond to? Then just do some elementary geometry and you have an answer.