It is known that any set of commuting diagonalizable matrices is simultaneously diagonalizable. So, it would be nice to ask the following generalization:
Given a monoid $M$ (not necessarily a group), a commutative submonoid $N$ of $M$ (with the same identity, so $eMe$ for some idempotent $1 \ne e \in M$ does not count even if it happens to be commutative), and some subset $A$ of $M$ for which $\forall a,b \in A\, ab=ba$ and $\forall a \in A\, \exists p \in M^{\times}\, p^{-1}ap \in N$ (where $M^{\times}$ is the subgroup of invertible elements of $M$), is it in fact true that $\exists p \in M^{\times}\, \forall a \in A\, p^{-1}ap \in N$?
If not, is it true under some additional assumptions (e.g. $M$ is a group, $N$ is an abelian subgroup of $M$, or $A$ is finite)?
None of the conditions you give suffice; that's not going to work in general. Here is a counterexample with $M$ a group, $N$ an abelian subgroup, and $A$ finite.
let $M=S_6$, let $N=\{e,(12)\}$, let $A=\{(34), (56)\}$. Note the elements of $A$ commute with each other, and they can each be conjugated into $N$ (any transposition is conjugate to $(12)$). But the elements of $A$ cannot be simultaneously conjugated into $N$, because they only have one place to go, and so that would require $g(34)g^{-1}=g(56)g^{-1}$, which is of course impossible since conjugation induces a bijection.