I'll try to give a geometrical approach.
You are considering a polyhedron
$$
P = \{x \in \mathbb{R}^{n} \ | \ Ax \leq b \}.
$$
where $b \in \mathbb{R}^{m}$ and $A \in \mathbb{R}^{n \times m}$.
(I'm using $Ax$ and not $A^{T}x$ to match the dimensions in the OP).
The easy case: no degeneracy
Let's assume that
- there is no primal degeneracy, i.e., no constraints are redundant w.r.t each other, and
- $P$ is full-dimensional (non-empty interior)
Then, $P$ has exactly $m$ facets, with the $i$-th facet being described by the $i$-th constraint
$$
\sum_{j} A_{i, j} x_{j} \leq b_{i}.
$$
Now, let $M \in \mathbb{R}^{m \times m}$, and consider
$$
Q = \{x \in \mathbb{R}^{n} \ | \ (MA)x \leq Mb \}.
$$
Geometrically, 1. asks under which condition on $M$ we have $Q = P$.
If $Q = P$, then each facet of $P$ is a facet of $Q$, and vice-versa.
Thus, for every $i$, there exists $\sigma(i)$ such that the hyperplanes
$$
\sum_{j} A_{i, j} x_{j} \leq b_{i}
$$
and
$$
\sum_{j} (MA)_{\sigma(i), j} x_{j} \leq (M b)_{\sigma(i)}
$$
are (geometrically) identical.
Since the polyhedra are non-degenerate, the $i \leftrightarrow \sigma(i)$ mapping is one-to-one, i.e., $\sigma$ is permutation, which gives you permutation matrices.
Assume for simplicity that $\sigma$ is the identity.
From the identity between each pair of hyperplanes, you then get that $M$ is a diagonal matrix with positive coefficients.
To conclude, we get $M = D \times S$ where $D$ is diagonal with positive coefficients and $S$ is a permutation matrix.
Note that this result only holds under the above two assumptions.
The hard case: degeneracy
As it's already been pointed out, depending on the data, there may be arbitrarily many valid $M$. Essentially, any redundant constraints can be aggregated in any way you want, without changing anything to the feasible region.
If you can isolate a set of non-redundant constraints, then you might apply the above result, combined with some (positive?) combination of the redundant constraints.
Obviously, there may exist multiple sets of non-redundant constraints, and you will likely see a combinatorial explosion there.