$\newcommand{\Hom}{\operatorname{Hom}}$
Let $V,W$ be $d$-dimensional real vector spaces, $A,B \in \Hom(V,W)$.
Let us try to define a map $A \wedge B:\Lambda_2(V) \to \Lambda_2(W)$, by setting $$ A \wedge B (v \wedge w)=Av \wedge Bw. \tag{1}$$
(This imitates the standard construction $A \wedge A (v \wedge w)=Av \wedge Aw$).
The problem with $(1)$ is that $A \wedge B$ is well-defined only when $$ Av \wedge Bw=-Aw \wedge Bv \tag{2}.$$
This condition is equivalent to
$$ Av \wedge Bv=0 \, \, \text{ for every} \, v \in V \tag{3},$$
which is equivalent to $$ \dim({\operatorname{span}\{Av,Bv\}}) \le 1 \, \, \text{ for every} \, v \in V . \tag{4}$$
Questions:
$(1)$ While Condition $(4)$ is very "geometric" (the images of every vector lies on a single line), it is not clear to me how to check it in practice (it's not enough to check on basis vectors).
Are there any "nice" necessary or sufficient conditions for it to hold? ($A =\lambda B$ suffices of course, but this is very trivial).
Edit: It turns out (see my answer below) that if $\max(\operatorname{rank}(B),\operatorname{rank}(A)) \ge 2$ then it is necessary that $A$ is multiple of $B$.
If at least one of the ranks is zero, we are done (one operator is zero, the other can be chosen arbitrarily). Otherwise, $\operatorname{rank}(B)=\operatorname{rank}(A)=1$. This is still open for now.
$(2)$ In case where $A \wedge B$ is well-defined, does it have a "geometric meaning"? (The classic $A \wedge A$ represents the action of $A$ on $2$-dimensional parallelepipeds).
There's an alternative construction which always makes sense: map $v\wedge w$ to $$Av\wedge Bw+Bv\wedge Aw.$$ I suppose one gets that from "polarizing" the $\bigwedge^2A$ and $\bigwedge^2B$ where $\bigwedge^2A(v\wedge w)=Av\wedge Aw$: $$Av\wedge Bw+Bv\wedge Aw= \left(\bigwedge{}^2(A+B)-\bigwedge{}^2A-\bigwedge{}^2B\right)(v\wedge w).$$