As I say in my essay on Jon IV, I think Benjen cached that horn on the Fist because he was being pursued or had to go into hiding.
To explain your timeline questions: Benjen knew that someone would probably be sent out after him as indeed he had been after Wymar Royce, and the Fist is a natural point for the NW to gravitate to Beyond-the-Wall (hence its use as a rendezvous point for the Shadow Tower and Castle Black during the Great Ranging).
But to my eyes, the timeline problems are bigger if it’s not Benjen because then he disappears, does nothing, and then suddenly reappears in TWOW.