Suppose $A,B$ are commuting invertible matrices with a common generalized eigenvector $v$ with eigenvalues $a,b$ respectively. That is, suppose there exist positive integers $K,L$ such that $(A-aI)^K v= 0$ and $(B-bI)^Lv=0$. Is it true that there exists a positive integer $M$ such that $(AB-abI)^Mv = 0$?
A bit of context: I came across this while thinking about the analogous version of this for eigenvalues (when $K=1$ and $L=1$). This is easy to show. In fact, the above statement is also easy to show if only one of $K=1$ or $L=1$ is true (that is, $v$ is an eigenvector for one matrix and a generalized eigenvector for the other).
Proof: WLOG suppose $L=1$. Then we have \begin{align} (AB-abI)^Kv &= \sum_{j=0}^K {K \choose j} A^{K-j}B^{K-j}a^jb^jv\\ &= \sum_{j=0}^K {K \choose j} A^{K-j}a^jb^Kv\\ &= b^K(A-aI)^Kv\\ &= 0 \end{align}
A natural question: is it true if $v$ is a generalized eigenvector for both matrices?
Yes. We can proceed as follows.
Begin by reframing the question: if $PQ = QP$ and $K,L$ are such that $P^Kv = Q^Lv = 0$ and if $a,b$ are arbitrary scalars, then does there necessarily exist an $M$ such that $$ ([P + aI][Q + bI] - ab I)^Mv = 0? $$ Note that $$ [P + aI][Q + bI] - ab I = PQ + bP + aQ. $$ Now, take $m = \max\{K,L\}$ and $M = 2m-1$; note that $P^mv = Q^mv = 0$. Apply the multinomial theorem: $$ (PQ + bP + aQ)^Mv = \sum_{k_1 + k_2 + k_3 = M} \binom{M}{k_1,k_2,k_3} a^{k_3}b^{k_2}P^{k_1+k_2}Q^{k_1+k_3}v \\= \sum_{k_1 + k_2 + k_3 = M} \binom{M}{k_1,k_2,k_3} a^{k_3}b^{k_2} Q^{k_1+k_3}P^{k_1+k_2}v. $$ Now, for all triples of non-negative integers $k_1,k_2,k_3$ with $k_1 + k_2 + k_3 = 2m-1$, we see that $k_1 + k_2$ and $k_1 + k_3$ are non-negative integers with sum greater than or equal to $2m-1$. It follows that either $k_1 + k_2 \geq m$ or $k_1 + k_3 \geq m$. In either case, we find that $$ P^{k_1+k_2}[Q^{k_1 + k_3}v] = Q^{k_1+k_3}[P^{k_1+k_2}v] = 0. $$ Thus, the above expansion of $(PQ + bP + aQ)^Mv$ must be equal to zero.