This is a continuation of Classification of algebras of finite global dimension via determinants of certain 0-1-matrices but this time with a concrete conjecture and using the simplification suggested by user esg to make the problem more compact.

Let $n \geq 4$ and $w \in \{3,4,...,n-1 \}$. Let $Z$ be the matrix of the cyclic shift (the companion matrix of $X^n-1$), and for non-zero $\mathbf{v}\in \{0,1\}^n$ let $\mathrm{diag}(\mathbf{v})$ be the diagonal matrix with $\mathbf{v}$ on the diagonal, and $M_\mathbf{v}:=I + Z+ \ldots + Z^{w-1}-\mathrm{diag}(\mathbf{v})$.
For fixed $n$, call the tuple $(w,v)$ perfect in case $\det(M_\mathbf{v})=(-1)^{(w-1)(n-1)}$.

Define $G_n := \{ w \in \{3,4,...,n-1\} | $there exists a nonzero $\mathbf{v}\in \{0,1\}^n$ with $(w,v)$ perfect $\}$.

It is an interesting question what the set $G_n$ is explicitly but my first guess was wrong and it seems that $G_n$ is complicated to describe for large $n$.

But here are two conjectures that would be nice in case they are true:

Conjecture 1: Maximum($G_n$)=$\frac{n+2}{2}$ in case $n$ is even and Maximum($G_n$)=$\frac{n+1}{2}$ in case $n$ is odd.

Conjecture 2: a) For $n$ even the number of perfect tuples $(w,v)$ with $w=(n+2)/2$ is equal to $\frac{3^{n/2-1}+1}{2}$ when we identify two tuples $(w,v_1)$ and $(w,v_2)$ when $v_1$ is a cyclic shift of $v_2$.

b) For $n$ odd the number of perfect tuples $(w,v)$ with $w=(n+1)/2$ is equal to $n-1$ when we identify two tuples $(w,v_1)$ and $(w,v_2)$ when $v_1$ is a cyclic shift of $v_2$.

The conjectures are tested with the computer for $n \leq 18$.