- Does it mean $\frac{d \langle \hat{X}^2 \rangle}{dt}$?
No. Suppose we have $\hat{H}$ and an observable $\hat{A}$ both independent of time, from the Schrodinger equation $\frac{d}{dt}|\psi(t)\rangle=\hat{H}|\psi(t)\rangle$ we have
$$\frac{d}{dt} \langle \psi(t)| \hat{A} |\psi(t)\rangle = \frac{\text{i}}{\hbar}\langle \psi(t)| [\hat{H},\hat{A}] |\psi(t)\rangle $$
If $\hat{A}=\hat{X}$ then we recover your first identity. But if $\hat{A}=\hat{X^2}$, you can easily compute the commutator and realize it is not $\hat{V}^2$.
- What is meant by $\langle \hat{V}^2 \rangle$?
The mathematical definition of $\langle \hat{V}^2 \rangle$ is given on the first line provided $|\psi(t)\rangle$ is normalized, and can be computed, for example, in the momentum basis as the last two lines
\begin{align*}
\langle \hat{V}^2 \rangle &=\langle\psi(t)| \frac{\hat{P}^2 }{m^2} |\psi(t) \rangle \\
&=\int_{-\infty}^{\infty} dp \langle\psi(t)|p\rangle \langle p| \frac{\hat{P}^2 }{m^2}|\psi(t)\rangle\\
&=\int_{-\infty}^{\infty} dp |\langle p|\psi(t)\rangle|^2 \frac{p^2}{m^2}
\end{align*}
The last expression tells you what it means: If you assume a large collection ($N \longrightarrow \infty$) of systems each one in the state $|\psi(t)\rangle$ and measure the momentum (or the velocity) you can get its distribution, $|\langle p|\psi(t)\rangle|^2$, which then allows you to get the average of squared velocity.
Additionally this average is related to the average kinetic energy since
\begin{align*}
\langle \hat{T}\rangle = \frac{1}{2}m \langle \psi(t)|\hat{V}^2 |\psi(t)\rangle
\end{align*}
and satisfies the energy conservation. For $\hat{H}=\frac{\hat{P}^2}{2m}+ V(\hat{X})$ we have the average
\begin{equation}
\langle \psi(t)|\hat{H}|\psi(t)\rangle=E=\langle \psi(t)|\frac{\hat{P}^2}{2m}|\psi(t)\rangle+\langle \psi(t)|V(\hat{X})|\psi(t)\rangle
\end{equation}