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Example. In 1941 Staling was (arguably) still thinking of Germany as a friend of sorts and (again arguably) would not likely attack without provocation. Can Germany run a Med campaign in North Africa and such to drive out the UK without the soviets attacking automatically in '41 because there is supposed to be a war in '41 between the Germans and Soviets?
Can Germany and the Soviets stay allied longer - say into late 42 or even 43?
In 1939 the Soviets invaded Poland too. What if the allies attack them - or is this even possible?

Allies can't attack them but barbarrossa can cetainly be delayed up until winter of 43 i think. The russians will only get stronger the longer you wait though. I have won a couple of games with a quick sealion and then turning on russia once england has been defeated.

There is strong evidence that Stalin planned to attack Hitler in 1942 or 1943. Although this plan is mentioned in several places, I can recommend Brian Fugate's "Operation Barbarossa" (Presidio Books, 1984) in particular as an interesting read, especially if most of your history reading was books based on Guderian as the primary source.

Stalin didn't think of Hitler as an allies nor the reverse; both in 39 were just wanting to postpone (for different reasons) a war they both thought inevitable. They just signed on how to share Poland ...
Currently WaW enforces war entries through the "freezing" system, one can tinker with that in the data files and allow for shorter or longer frozen periods. What is not possible is to allow "dynamically" (ie in game as opposed to predefined by scenario) players to choose their sides - I'm not sure either if it's possible by scenario setup to have USSR join Axis for example.