Let $V$ be a finite dimensional representation of $\mathfrak{sl}(2, \mathbb{C})$. Then it has operators $E, F, H$ such that $HE - EH = 2E, HF - FH = -2F, EF - FE = H$. Let $\bar{V}(\lambda)$ represent the generalized eigenspace corresponding to $\lambda$ for some linear map.
I can show the following facts. If $\lambda$ is an eigenvalue of $H$ with maximal real part, then $E$ restricted to $\bar{V}(\lambda)$ is the zero map. If $v \in \ker E$ is non-zero, then $E^k F^k v = P_k(H) v$, where $P_k(H) = k! H (H - 1) \cdots (H - (k - 1))$. If $v \in \bar{V}(\lambda)$ of $H$ for any choice of $\lambda$, then there exists a $N > 0$ such that $F^N v = 0$.
I am next asked to show that $H$ is diagonalizable on $\bar{V}(\lambda)$ (of $H$) by utilizing the fact that $P_k$ does not have repeated roots and computing $E^N F^N v$, where $N$ is picked as defined previously. In particular, I can show that if $v \in \bar{V}(\lambda)$ is non-zero and $(H - a_1) \cdots (H - a_n) v = 0$ and the $a_i$ are pairwise distinct, then there exists an $i$ such that $a_i = \lambda$. EDIT: the $a_i$ do not necessarily have to be distinct, but they are in $P_k(H)$.
I am then not quite sure how to proceed. There is a condition for calculating $E^N F^N v = 0$ with $P_k(H)$, which is that $Ev = 0$, but this is not necessarily true, because $Ev \in \bar{V}(\lambda + 2)$ if $v \in \bar{V}(\lambda)$. I have tried further examining the identity $$ E^k F^k - E^{k - 1} F^k E = k (H - (k - 1)) E^{k - 1} F^{k - 1}, $$ but to no avail.
However, if we can force the evaluation of $E^N F^N v = 0 = P_k(H) v$, then we know that $\lambda$ is one of $0, 1, \dots, N - 1$. Furthermore, since the $H - a_i$ all commute with each other, we can see that $k! [\prod_{i \neq \lambda} (H - i)] (H - \lambda)v = 0$. If $(H - \lambda)v \neq 0$, then one of the $i$ must be equal to $\lambda$, which is obviously false. Thus $v$ is an ordinary eigenvector of $H$, so $H$ is diagonalizable on $\bar{V}(\lambda)$, where it can be represented as $\dim \bar{V}(\lambda)$ entries of $\lambda$ on the main diagonal.
It seems you have answered your own question. If I read correctly the only thing you need is that $E^NF^Nv = 0$ but this follows immediately from the result $F^Nv = 0$ you already have.