When people talk about the logistical limits on the size of medieval armies, are they primarily talking about limits to the number of men you can plausibly raise from a given area (so, with enough land, a medieval European state could have raised an Umayyad-sized army) or is it the difficulty of organizing the supply chain to feed everyone? If the latter, were the Umayyads simply better at requisitioning and managing the supplies than a medieval European-style state?

Both, although the two affect one another. 

The Ummayads had the advantage of having absorbed the highly efficient Byzantine administrative system when they conquered Egypt and Palestine and Syria, and the also quite good bureaucracy of the Persians when they took Persia. Also, the east had historically been much much richer than the west, so they had more GDP per capita to tax from. 

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