This question made me think of a related question:
Suppose we have a sequence $a_n$ and a set of permutations $S$ with $|S| = N$ (for some $N > 1$). Suppose that, for any two (distinct) permutations $\sigma$ and $\phi$, both in $S$, we have $$ \sum_{i=1}^\infty a_{\sigma(i)} \ne \sum_{j=1}^\infty a_{\phi(j)} $$ In other words, the rearranged sums of $a_n$ under the permutations in $S$ are all pairwise distinct. In addition, at most one of these rearranged sums diverges.
(NB: The identity function may be a member of $S$, but is not necessarily. WLOG we can always reformulate the problem so that it is.)
If $N = 2$, does this imply $a_n$ is conditionally convergent and can be rearranged to any value? If not, is there some larger value of $N$ which yields this implication, or do we need to have some stronger condition to establish conditional convergence?