The Dirac field may be re-interpreted as a "second quantization" of a single particle theory with Hamiltonian $H_d$. There are two ways to do so. Firstly, the observation you made above: the field respects a Schroedinger-like equation with $H_d$ as Hamiltonian and therefore you may consider the state $\psi (x) = \Psi(x) |vacuum \rangle $ (I used $\Psi$ to denote the field, $\psi$ to denote the wave-function) as a genuine wave-function. Secondly, as remarked below, you may write the Hamiltonian of the Dirac field in a way that suggests a second-quantization formulation of a many-body operator: $\mathcal{H} = \int \bar{\psi} H_d \psi$.
However, this interpretation poses a problem: the Hamiltonian $H_d$ is not positive definite. In fact, for every state of positive energy you also have one with the opposite energy. This problem may be overcome by requesting that the vacuum state is the one with all the negative energy states filled up. Because we are dealing with fermions, those state are effectively ruled out, and we are left with positive energy states. (This was the original interpretation given by Dirac, the "Dirac sea").
Now, this is a little bit artificious, and not necessary. In fact, as you already saw, if you follow the "Canonical Formalism" approach, starting from the Lagrangian you get to a different Hamiltonian $\mathcal{H}$ which is manifestly positive since is written as the sum of operators $a^{\dagger} a$ with positive coefficients (which are the energies).
In this interpretation, you see the Dirac theory as a second quantization of states with definite quadri-momenta and spin-half, together with their "anti-particles", and you give up on any interpretation of $\psi$ as a wave-function. This is customary in QFT: you don't have a position operator and a wave-function $\psi(x)$. Instead, the observables you consider are just quadri-momenta, spin and helicities.
Now, to explicitly address your questions:
1) I would say that this procedure is not completely legit, because it gets you to the negative energy states, a problem solved in artificious way with the Dirac sea. Moreover, the canonical formalism is a (more or less) automatic machinery that when fed with a Lagrangian will give you canonical variables written as sums of single-particle creators/annihilators and a positive Hamiltonian build with these variables. It always works, and does not requires you to put extra efforts in interpreting its results (like the Dirac sea), so why should we bother with other interpretations?
2) I guess the two are not strictly related. $p_i$ is a single particle operator, you may use it to define a translation operator in the fock space and I guess you obtain something like $P = \sum_p p a_p^{\dagger} a_p$. $\pi$ is just the variable canonically conjugate to $\psi$, it has a "x" dependance and its expansion on $a,a^{\dagger}$ does not contain their products. Hence the $p_i$ (and $P$) is not related to $pi$. For $H_d$ and $\mathcal{H}$, the two are related by $\mathcal{H} = \int \pi H_d \psi$. (See Weinberg, vol 1, pag 323).