As the Question asks about "attempting to find... the linear transformation in $\mathbb{R}^{300}$ that most closely maps a set of pairs of vectors to each other," let me propose a computational approach based on @joriki's analysis of possible solutions to $A^2 = I$.
Suppose that we have a finite set of vectors and their images $(u_i,Au_i)$. If there were enough vectors $u_i$ to span $\mathbb{R}^{300}$, these pairs would exactly determine the matrix $A$.
Since the matrix we want must satisfy $A^2 = I$, its construction depends on a choice of subspaces $U_0,U_1$ such that $U_0 \oplus U_1 = \mathbb{R}^{300}$, where $U_0$ is the eigenspace of $A$ corresponding to $\lambda = -1$ and $U_1$ is the eigenspace corresponding to $\lambda = 1$.
In exact arithmetic $(I-A)/2$ would be a projection onto $U_0$ and $(I+A)/2$ a projection onto $U_1$. It may be possible to precisely recover a spanning set $v_i = (u_i - Au_i)/2$ for $U_0$ and a spanning set $w_i = (u_i + Au_i)/2$ for $U_1$ even if the $u_i$ do not fully span $\mathbb{R}^{300}$.
Since $U_0 \cap U_1 = \{0\}$ by design, our goal is to extract the "best" basis for $U_0$ from vectors $v_i$ and basis for $U_1$ from vectors $w_i$ subject to having a combined dimension $300$ and linear independence.
A naive approach would be to perform row reduction on matrix $V$ consisting of rows $v_i$ and on matrix $W$ consisting of rows $w_i$. In the presence of rounding errors caused by floating point arithmetic, a more accurate determination of rank for $V,W$ can be achieved by orthogonal transformations rather than elementary row operations. See QR factorization and consider the results applied to $V,W$ to obtain the best combination of bases with dimension $300$.
Studies in the literature of the best rank-finding orthogonal algorithms often include the phrase "rank-revealing QR".