re: Do you think the Allies would have won WWII if Russia has sided with Germany?

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THE reason why Germany invaded Russia was to seize the Caucasus oilfields. They had none of their own (they made synthetic fuel from coal) and their Romanian supply was insufficient. They wouldn’t be able to carry on, much less invade Britain, without an oil supply.

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This is false. The reasons for attacking the USSR were multiple, but a necessity to attain the oilfields of the Caucasus or else the Germans would be incapable of successfully prosecuting the war against Britain is false.

First of all, obviously carrying out a war against the USSR would only stretch German oil supplies even thinner, along with putting tremendous strain on their manpower and equipment and would severely limit their operations against the British during the time such an invasion was being carried out. Also, as we know, the Germans did not acquire the oilfields of the Caucasus yet were still able to very capably attack and resist on multiple fronts even from June of 1941 through April 1945 (duration of war with Soviets). Thus if they had adequate oil supplies to conduct the entirety of their fighting in the Second World War without acquiring any Caucasus oil, it is rather presumptive and counterintuitive to suggest that they didn't have adequate oil supplies to carry on a limited war against the British Empire after knocking out one of their most feared foes, France, in just 6 weeks and thus preserving tremendous resources and manpower in the process.

Germany invaded the USSR because Hitler's ultimate ambitions were always Eastern expansion at the expense of the USSR and the Slavs. Part of the reason was simply Hitler's view of a German Empire in the East. Politically, this allowed for the destruction of Bolshevism, which likewise served the ideological ends of Hitler and the Nazi philosophy. Thirdly, it would solidify Germany's access to foodstuffs as well other natural resources, oil included. Manpower from forced labor could be allocated. But perhaps most practically for the current war aims, eliminating the USSR in one fatal blow would effectively eliminate all hope in British political circles for a victory over Germany and would force them to reach a settlement. Hitler had little ambition to destroy the British Empire and always preferred a settlement in which both coexisted as the major European hegemonic powers.

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It was a hail mary to begin with because the Germans were already limited on fuel and faced other major supply problems. They were on a tight timeline before they ran out.

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What was their timeline exactly? How were they threatened after the fall of France, timeline wise, by a shortage of oil such that they were running out of time to fight the British?

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they stretched out the German supply lines beyond what they could handle and drug out the timeline beyond the oil supply collapse deadline.

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Which could have been avoided entirely by not invading the Soviet Union, which indicates that the rationale for doing so was something other than an imminent, desperate, and suicidal drive for oil. They only served to deplete their supplies more so as well as losing equipment and men to both breakdowns, destruction, and death as well as strategic consumption necessary to occupy, control, and maintain supply lines across such mass expanses as the USSR. Again, it's counterintuitive to do all this simply to drive on Soviet oil deep in the Caucasus. All this to prosecute a war against the British in North Africa and the British Isles?

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The Germans tried to push on to Grozny and Astrakhan the next summer.

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Yes, now that the Germans had embroiled themselves in a massive, drawn out, two front war in which they now faced the entire might and resources of not just the Soviet Union, but now the United States as well. Now their limited oil supply was REALLY a strategic problem, whereas in July/August of 1940, when only the British Empire stood as Germany's wartime foe, it was of minimal strategic threat to the German war economy.

Also, the fact that these oil fields were not a principal objective in the initial Barbarossa campaign but were only the objectives of the following year's campaign indicates that securing oil in order to bolster desperately low supplies as a necessity to continuing any prosecution of the war was NOT the motivating factor of launching the invasion of the USSR. Otherwise, not acquiring them in the initial campaign would have caused an imminent collapse of the German war machine. It of course didn't.

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though you could say neither nation strategically had any other choice.

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Strategically, the Germans had MUCH better choices than invading the USSR to bolster oil supplies. The primary "strategic" reasons to invade the USSR in 1941 were 1) to stave off a potential Soviet invasion of Germany and her eastern allies while tied down fighting the British (a situation in which the USSR could have ACTUALLY crippled Germany's oil supplies by taking the Romanian oilfields) and 2) as a means to knock out the only remaining European state that could potentially join the war effort and fundamentally threaten Germany's strategic advantage over the British Empire given the fall of mainland Europe. Bolstering oil and other resource acquisition was secondary to these first two, primary strategic concerns.

Personally, I'm of the opinion that the invasion of the USSR was entirely rational and justifiable on the basis of preventing a sudden Soviet attack which could have instantly threatened Germany's entire position in the war. Even as favorable as it appeared to be at that time, Germany's strategic position was highly vulnerable in the East given Soviet proximity to Germany proper as well as the Ploesti oilfields. Hitler's reasoning though, as mentioned above, was multiple. It certainly wasn't necessary for the Germans to secure their strategic wartime positioning against Great Britain. The British were in very poor shape to conduct much more than defensive operations against the Germans at this time.