Let $G$ be a Lie group and $\pi : G\to GL(V)$ a finite-dimensional representation of $G$ in the vector space $V$. For every $g\in G$ we have a linear transformation $\pi(g) : V\to V$. Being linear, if we give a basis $\{E_a\}$ of $V$ we can associate a matrix to $\pi(g)$: $$\pi(g)E_a = \pi_a^{\phantom{a}b}(g) E_b\tag{1}$$
Linearity of $\pi(g)$ then allows us to do the following: $$\pi(g)v = \pi(g)[ v^a E_a]=v^a \pi_a^{\phantom{a}b}(g)E_b\tag{2}$$
So if we agree that the components are all in the same basis, $\pi(g)$ takes a vector $v$ with components $v^a$ to a vector $\pi(g)v$ with components $$[\pi(g)v]^b=v^a\pi_a^{\phantom{a}b}(g)\tag{3}.$$
Now it is then common in Quantum Mechanics that we wish to see a tuple of $\dim V$ operators, $A^a$, as a sort of "operator-valued elements of $V$". In other words, it seems we would like to make sense of something of the form $$A = A^a E_a\tag{4}$$
and allow $\pi(g)$ to act upon $A$ to produce $\pi(g)A$.
What one usually does is demand there be a unitary representation $\Pi : G\to {\rm U}({\cal H})$ with the property that: $$\Pi(g)^{-1}A^b\Pi(g)=A^a \pi_a^{\phantom{a}b}(g)\tag{5}.$$
What is the proper mathematical way to say that a tuple $A^a$ are the components of a single "operator-valued element of $V$" $A$ as in (4)? This seems not obvious to me because (4) is meaningless since operators $A^a$ cannot multipy the basis vectors $E_a$ of $V$.
Moreover, (5) does not seem as such a definition for me. The vector space $V$ is independent of the representation. So we should first be able to define what an "operator-valued element of $V$ is* (make sense of (4)) and later tell how $\pi(g)$ can act on such objects (make sense of (5)).
Given that we know how to make sense of an "operator-valued element of $V$" why intuitively is (5) the right way to allow $\pi(g)$ to act on such objects? Eq. (5) seems to be saying that the components of $\pi(g)A$ are $$[\pi(g)A]^b= \Pi(g)^{-1}A^b \Pi(g).$$
Why this is the right way to allow a representation $\pi : G\to GL(V)$ on $V$ to act on operator-valued vectors in $V$?
My guess for (1) is that an operator-valued element of $V$ should be a tensor product: $$A = A^a\otimes E_a$$
and that we should take $\pi(g)$ to act upon it by acting on the $V$ factor: $$\pi(g) A = A^a\otimes \pi(g)E_a = (\pi_a^{\phantom{a}b}(g)A^a)\otimes E_b,$$
but then again, I don't see why we should demand there be a unitary representation $\Pi(g)$ so that (5) holds.