Let us drop the calculations and formalism for a minute, and think about this problem geometrically.
We know the eigenvectors $v_1, ..., v_n$ are orthogonal, and correspond to $n$ points on the unit sphere, i.e. $\forall j,\ \|v_j\| = 1$. Since $u_0$ also has norm 1, the function $H_j(0)$ is the cosine of the angle $\alpha_j(0)$ between $u_0$ and $v_j$ [1]:
$$
H_j(0) = u_0\cdot v_j = \|u_0\|\|v_j\|\cos\alpha_j(0) = \cos\alpha_j(0)
$$
Now consider the ODE for $H_1$:
$$
H_1^\prime(t) = 2H_1(t)\sum_{i=1}^n (\lambda_i - \lambda_1)H_i(t)^2
$$
For $u_0 = v_1$, we have $H_1(0) = 1$, and since the eigenvectors are orthogonal $H_i(0) = 0$ for all $i > 1$. Hence $H_1^\prime(0) = 0$, and it follows that $H_1^\prime(t) = 0$ for all $t$, i.e. $v_1$ is an invariant. Furthermore because in this case $H_1(t)=1$ is maximal, we have $\tau_\varepsilon = 0 < n^{2/3}$, and at least one counter-example to the proposition [2].
However to disprove the proposition, a single counter-example is not sufficient (the measure of a finite set is zero). Next we will show that $\tau_\varepsilon < n^{2/3}$ in a neighborhood of $v_1$ for any threshold $\varepsilon$ and dimension $n$.
Pick a threshold $0 < \varepsilon \leq 1$. Since $\lambda_i - \lambda_1 \geq 0$ for all $i$, all of the terms in the formula of the derivative $H_1^\prime$ above are non-negative, and therefore if we pick $u_0$ such that $H_1(0)\geq 0$ we have:
$$ \forall t\geq 0,\ H_1(t)\geq H_1(0) = \cos\alpha_1(0) $$
Hence for any choice of $u_0$ at a small enough angle from $v_1$ such that $0\leq \alpha_1(0) \leq \cos^{-1}\varepsilon$, we have:
$$
\forall t\geq 0,\quad H_1(t)\geq H_1(0) = \cos\alpha_1(0) \geq \varepsilon
\quad\implies\quad
\tau_\varepsilon = 0
$$
proving that $\tau_\varepsilon < n^{2/3}$ occurs with non-zero probability for any dimension $n$ and threshold $\varepsilon$, i.e. $P( \tau_\varepsilon < n^{2/3}) > 0$.
[1] Note that the only way to satisfy the assumption $\sum_{i=1}^nH_i(t)^2 = 1$ for all $t$ is to allow $\| u_t \| \leq 1$. So in general $H_j(t) = \|u_t\|\cos\alpha_j(t)$.
[2] Naturally I am assuming $\varepsilon \leq 1$.