Great thread, very interesting read.
Shfting the focus a bit to the Soviets as well as from strictly military considerations to an interesting notion on societal considerations, industry and potlitics that are major reasons for the Soviets capability of continuing resistance, simply because I find it a missing field in this thread.
What we have to remember with the German miscalculation, besides the number of Soviet divisions, logistics, infrastructure as have already been brought up.
The Germans severely underestimated the 'national unity' and the political stability of Soviet society. We have to remember that this was a people who had been subjected for 2 decades with several political campings in an effort to create "the soviet man". Its wrong to see that as an empty maxim simply done by the communist party, the strive for political indoctrination seems by most accounts to have had a great effect. Naturally not as complete as the Soviet authorities or defenders would have you believe.
I saw someone earlier in the thread commenting that the Soviet civilian population was just like westerners, but this would in my mind be to make the same flaw that the Germans did in 1941.
The earlier 5-year plans, heavy political campaigning, terror, for more than a decade had made it a norm for the civilian population to accept sever hardships in the service of the state. We see people quite quickly singing up en masse, we see for the major parts of the war people working 10-12hr shifts in crudely constructed (or not even fully constructed) factories. Living of very little food and huge amounts of people living in earthen dugouts. Even with these conditions dissidence doesn't seem to ever become a major issue. Like someone said earlier in the thread, the dissident existing in the last two decades of the USSRs existent simply was not a factor during the war years.
For a better look at specifically the work of the soviet homefront during the war (and before that) I recommend Lennart Samuelssons "Tankograd"
The strong political indoctrination that was a result of the communist experiment will also help to explain the question of why the soviets seemed to have such greater reserves of manpower compared to the Axis, even though this difference is much greater than simple demographics can show you. The Soviets where simply able to quickly mobilize a huge amount of their population for the war-effort, and people accepted very sever hardships. This is where you get the great difference in available manpower.
From my understanding the Germans ultimately bet that the destruction of the RKKA west of the Dniepr, in a few lighting campaigns would show the weakness of the Soviet regime to the soviet population and this in turn would create political turmoil against the regime. Which in turn would lead to a breakdown in effective resistance, soviet infighting and a possible peace deal with whatever government remained in power.
For you guys wondering WHAT the Germans where thinking, with all the obvious problems of logistics etc. I think the German high command betting on a similar outcome to the Russian defeat in WW1 seems like a plausible one.
From a 'political' point of view this is Germanys critical mistake, the Soviet people where never really going to throw in the towel.
Deduction on possible German reasoning is my own but the info you'll get from plenty of authors writing about civilian, political and industrial history of the USSR. Samuelsson does a great job with that, Alexievitchs books are very much just about stuff like that. Not sure about more stuff published in english though.
Just wanted to give a bit of different perspective from the regular military one. Naturally as many of you have you can explain the failure of Barbarossa with many factors and perspectives but I just wanted to introduce another one. Im often disheartened by how some authors leave out quite important things or frankly have poor knowledge on the more societal/political part of the war, even good ones.
@Oakfan I suspect your original view of the Political Commissar role might have come from bunching them in with the "Special departments", the NKVD staff that where set to keep tabs on the army.

Its a common mistake. But NKVD troops in the army and Political Commissars are two different institutions.