David Stahel: Operation Barbarossa and Germany's Defeat in the East is a great study that shows the failure of Operation Barbarossa and how it doomed Germany.
This video is a very good summarised version of David Stahel's book Operation Barbarossa and Germany's Defeat in the East first chapters.
This is very good, planning and early stage of Barbarossa:
https://www.amazon.co.uk/Operation-Barbarossa-Germanys-Cambridge-Histories/dp/052117015X
Stahel's book is good
>Did Germany delay, or hasten their advance into Russia? Could they have effectively attacked sooner (perhaps before Russian tank factories were quite so productive), or did they invade sooner than was wise?
No, they could not have attacked before late June because of the late rainy season.
>Perhaps one way of removing some of the inherent hand-waviness from my question is to consider when and why Hitler argued with his generals over these moves (I assume in these cases Hitler was strategically wrong).