This answer nicely categorises which permutations of a finite set have square roots. This prompts the following question:
Does every permutation $\sigma:\mathbb{N}\to\mathbb{N}$ that contains no finite cycles (i.e. it is "finite-cycle-free") have a square root?
Finite-cycle-free permutations can be generated by using a double (two-way) greedy algorithm that avoids cycles.
For example, $\sigma(1) = 2,\ \sigma^{-1}(1) = 3,\ \sigma(2) = 4,\ \sigma^{-1} (3) = 5,\ \sigma(4) = 6,\ \sigma^{-1} (5) = 7,\ldots. $
You can generate other finite-cycle-free permutations by choosing larger numbers, in other words, the algorithm doesn't have to be greedy. For example, $\sigma(1) = 12,\ \sigma^{-1}(1) = 27,\ \sigma(2) = 400,\ \ldots. $ But you must avoid cycles.
Anyway, the question above is what I am interested in. I haven't found a square root for the greedy algorithm in the first example. So maybe there isn't one, but right now I don't see a reason why this would be the case.