This is a partial answer I hope will provide a useful starting point. I confirmed the asker's numerical observations with the web version of Mathematica function evalution and the Keisan high-precision calculator. I found a recent paper which gives information in its introduction that also confirms the asker's conjecture:
Ian Thompson, "Algorithm 926: Incomplete Gamma Functions with Negative Arguments", ACM Transactions on Mathematical Software, Volume 39, Issue 2, February 2013, Article No. 14
This article is concerned with the computation of $\gamma (n+1/2,−x)$,
where $n$ is an integer and $x>0$. It turns out that these are purely
imaginary quantities, and so, once the lower function is computed,
$\Gamma(n+1/2,−x)$ can be obtained from (3) without the loss of any
significant digits.
The referenced equation (3) is the well-known identity $\gamma(a,t)=\Gamma(a)−\Gamma(a,t)$. The paper doesn't go into details as to why $\gamma(n+1/2,-x)$ is always a purely imaginary quantity (at least not in any form that I, as a non-mathematician, recognize as such). It provides the following expansion which may be useful:
$$
\begin{align}
S_{n}(x) = e^{-x} \sum_{j=0}^{\infty} \frac{x^{j}}{j!(n+\frac{1}{2}+j)}, \enspace \enspace n \in{}\mathbb{Z}, \enspace x \ge 0, \\
\gamma(n+\frac{1}{2},-x) = i(-1)^{n}e^{x}x^{n+1/2}S_{n}(x).
\end{align}
$$
It also notes the recurrence relation
$$(n+\frac{1}{2})S_{n}(x) + xS_{n+1}(x)=1.$$