This is strongly linked to this previous question of mine.
In this question I am trying to show that $$\frac{\hbar}{\sqrt2}\left(i g_z \pm g_y\right)=\pm\frac{\hbar}{\sqrt{2}}\left(g_y \pm ig_z\right)\tag{*}$$
From $(*)$; it seems that factoring $\pm$ out of the bracket did nothing other than switch the sign of the terms in the bracket. If this is true; then it must be the case that $$\pm(\pm 5) = 5\tag{a}$$ & $$\pm\left(\pm \left(\pm 8\right)\right)=-8\,\tag{b}$$ and for my specific case $$\pm\left(\pm \,i g_z \right) = ig_z\tag{c}$$
It's not obvious to me why $(\rm a)$, $(\rm b)$, $(\rm c)$ are true; if I had to guess I would say it's because the $$+\times +=+$$ & $$- \times - = +$$
Is there a better way of thinking about this or am I on the right tracks?
The $\pm$ sign stands for $+$ or $-$.
(In my opinion, it should be avoided as much as possible, since it is likely to cause confusions like this one.)
So you can answer your question by considering each time the two cases :
$$\begin{cases} \text{when $\pm$ stands for $+$} \\ \text{when $\pm$ stands for $-$}.\end{cases}$$
So you indeed have
$$\frac {\hbar }{\sqrt 2} (ig_z+g_y)=+\frac {\hbar }{\sqrt 2} (g_y+ig_z)$$
and also
$$-\frac {\hbar }{\sqrt 2} (ig_z+g_y)=-\frac {\hbar }{\sqrt 2} (g_y-ig_z)$$
so your equality is true for $\pm$.
It is the same for all the other examples you gave, and you can see that
$$\pm(\pm 5)=5$$
and
$$\pm(\pm(\pm 8))=\pm 8.$$