Let $D$ be an integer greater than 1. What is the largest number $N$, such that for all sets of $N$ Hermitian $D\times D$ traceless matrices $M_i$, $i=1,\dots,N$, there exists a non-zero complex vector $v$, such that $v^HM_iv = 0$ for all $i$? ($v^H = (v^*)^T$ is the conjugate transpose).
Example. For $D=2$, $N$ must be less than 3, because for a set $M_i = \sigma_i$, $i=1,2,3$, where $\sigma_i$ are the Pauli matrices, for any vector $v$: $$ \sum_i (v^H M_i v)^2 = \Vert v\Vert^4 \neq 0\,, $$ so $v^H M_i v$ cannot all simultaneously vanish. However, for $N=2$ it is possible: let $v_1,v_2$ be eigenvectors of $M_1$ with eigenvalues $\lambda,-\lambda$. Then for $v = v_1 + \alpha v_2$, with $|\alpha| = 1$, $v^H M_1 v = 0$. Then $$ v^H M_2 v = \alpha (v_1^H M_2 v_2) + \alpha^{-1} (v_2^H M_2 v_1). $$ Then any solution to $\alpha^2 = -(v_2^H M_2 v_1)/(v_1^H M_2 v_2)$ will satisfy $v^H M_2 v = 0$. Thus $N=2$ is the answer.
Conjecture (false). For any $D$, $N$ is upper-bounded by $D^2-2$, because $D^2-1$ is the dimension of space of traceless Hermitian matrices, which for any $v$ contains $P_v - 1_{D\times D}/D$, where $P_v$ is the projector onto $\operatorname{span}\{v\}$, the Rayleigh quotient of which is $1-1/D\neq 0$. My conjecture is that $N = D^2-2$ is the correct answer.
Motivation. In quantum mechanics Rayleigh quotients $(v^HMv) / (v^H v)$ describe expectation values of quantum observables. The question then can be read: for a quantum system in $D$-dimensional Hilbert space, what is the maximum number of independent observables, that can have simultaneously vanishing expectation value.
New conjecture. As proven in @Nathaniel Johnston's answer and comments thereafter, the answer is bounded by $N < 2D - 1$. The current conjecture (checked numerically with random matrices) is $N = 2D-2$.