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Thanks again. I guess what I'm after is an intrinsic way to work out if $G/N$ is solvable, without actually knowing what $N$ is! I can actually reduce to ruling out the case where $G/N = A_5$, since, after enlarging $N$, $G/N\hookrightarrow\mathrm{Aut}(M_2(k)) = \mathrm{PGL}_2(k)$).
As you say, the situation is indeed simple in the finite case! In the infinite case, it comes down to whether $G/N$ has an index two subgroup. Is there any information that is intrinsic to the representation that I can make use of? I know nothing about $N$ a priori.
That's only true if $k =\mathbb C$ or a finite field. Typically, $k$ will be something like $\overline{\mathbb Q}_p$ for me, and the image won't be finite.
My motivation behind the question is this: I have a four dimensional representation $\rho$ which decomposes as $\sigma + \sigma$ after restriction to $N$. I only know that $N$ is a finite index subgroup, but nothing else. I'd like to know under what circumstances there exists an $H$ and a rep $\sigma'$ of $H$ such that $\rho =\mathrm{Ind}_H^G\sigma'$.
Thanks for your answer! I'm not sure the corollary helps: if $\mathrm{End}(\mathrm{Res}^G_H(V)) = k\times k$, then enlarging $H$ if necessary, $V=\mathrm{Ind}^G_H(U)$, where $U$ is one of the two distinct subreps. For any $g\in G$, wouldn't $\chi_V(g)$ usually (always?) be even?