A feature of Winston Churchill is that he liked to appoint officers who were friends of his or at least men he knew. Because of that, Churchill kept appointing Henry Maitland Wilson to various posts. We suspect that Thomas Blamey might have done better then General Wilson. The problem with General Blamey Churchill was that Blamey was an Australian and not a regular army officer. But what we know of his background, he performed better than we expected.
We saw, then, General Blamey making plans as corps commander. Then we saw General Wilson make plans without consulting General Blamey that totally undercut Blamey's plans. We can see now that General Wilson worked independently, since he was army commander, he figured that he could just go ahead and make plans without consulting his subordinates. We see that the Australian historian didn't like the command structure with Wilson issuing orders without consulting Blamey. The Australian historian felt that Blamey should have been the army commander, and in fact, Blamey would have been the logical choice.
Another Churchill choice, in choosing Bernard Freyberg to command the defense of Crete was also a mistake. By the time Freyberg reached Crete, he was in bad shape due to exposure and lack of rest. Freyberg seems to also have lacked the necessary experience to have commanded the defense. If we wanted to defend Churchill's choice of Freyberg, it would have to be on the basis of the immense prestige of Freyberg. Unfortunately, prestige was not enough to successfully command the defense of Crete.
As it was, Wilson's plan was a bad plan. Blamey's staff disagreed with the plan to split the force between the north side of the river and the south side. This is based on the account in "Greece Crete and Syria" by Gavin Long.