It appears that the answer is 'no', based on the answer to the OP's previous question, A question on eigenvalues. In the answers to that question, it is pointed out that there is a 1965 paper by Adams, Lax, and Phillips that implies that there exists a 5-dimensional subspace $W_0\subset V$ such that its nonzero elements are, in fact, nonsingular (which is considerably stronger than what the OP required).
If you let $\hat C\subset V$ denote the $12$-dimensional cone of Hermitian matrices with at least two zero eigenvalues, then the projectivization of $\hat C$ is a closed algebraic subvariety $C\subset\mathbb{P}(V)\simeq\mathbb{RP}^{15}$ of dimension $11$. By construction $\mathbb{P}(W_0)\subset \mathbb{P}(V)$ does not meet $C$. The set of subspaces $W\in\mathrm{Gr}(5,V)$ such that $\mathbb{P}(W)\cap C=\emptyset$ is therefore nonempty and it is clearly open in $\mathrm{Gr}(5,V)$ (because $C$ is closed). Therefore, in particular, it has nonzero uniform measure.
NB: The OP asked what I meant by 'near' in my comment above. If one fixes an inner product $q$ on $V$, say the obvious $\mathrm{U}(4)$ invariant one (but any positive definite inner product will do), then there is induced on each $\mathrm{Gr}(k,V)$ a natural metric, unique up to scale, that is invariant under the the orthogonal group of $q$. By 'near', I meant 'close in such a metric'.