OK--I apologize if this sounds far-fetched, but I was thinking if there is actually a very good analogy between the Hundred Years' War and the Eastern Front of World War II.
To elaborate on this, in both the Hundred Years' War (which, as far as I know, was actually a series of wars) and in the Eastern Front of World War II, a less populous country (England and Nazi Germany, respectively) was able to initially make very large territorial conquests in a much larger country (France and Russia, respectively). However, in spite of their very large territorial conquests, neither England nor Nazi Germany succeeded in achieving their ultimate war aims (conquering all of France and conquering the Soviet Union up to the Urals, respectively). Likewise, both France and the Soviet Union were eventually able to "regain their footing" and to use their numerical superiority (and presumably resource and logistical superiority as well) to push back against the English and Nazi German invaders and to eventually kick both of these invaders out of France and Russia, respectively. To my knowledge, after the English were kicked out of France and the Germans were kicked out of Russia, neither England nor Germany was ever able to pose a serious land-based threat to France and Russia, respectively.
Any thoughts on this analogy of mine?
Well, from my limited understanding of France in this time period; no.
Perhaps you can make some stretch that the relative disunity of France in the Hundred Year's War (HYW) is comparable to the initial confusion and disorder present in the RKKA, but I'd say its too much of a stretch. The disorder in the RKKA in 1941 is as much a result of purges and confusion as it is because of legitimate losses; the savagery and speed of the initial attack is as much to blame for the RKKA's condition in the first month of conflict as any pre-existing conditions.
Comparatively, France's disunity has far more to do with the fact that well....'nations' as we understand them simply didn't exist at this time. In terms of unity of command and concentration of forces, England's far greater unity gave it a de facto local superiority or at the very least parity in numbers.
In short, the political and other pre-existing conditions are in no way similar and its a gross misunderstanding of the politics of France in this time period to simply look at size and population and go 'France's military potential was infinitely greater than England's.'
Finally, the HYW in reality is a series of separate wars, and must be imagined in such a light. Several of these series of wars ended with treaties highly favorable to the English, and one can indeed safely conclude that the English Kings related to those treaties did accomplish many of their political goals.