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Is Leningrad actually likely to fall in this TL? Also, how many additional Soviet Jews are likely to succeed in evacuating to the interior of the USSR in this TL and thus to escape the impending Holocaust?

What about in terms of their overall advance?

Gotcha. BTW, how would Operation Barbarossa have turned out with Lend-Lease and with the Soviets controlling the General Gouvernment (minus Warsaw) at the start of Operation Barbarossa, in your honest opinion?

Does Moscow hold out in 1941, only to fall in 1942? BTW, might a realistic PoD for this be if the Soviet Union acquires and annexes the General Gouvernment (minus Warsaw, which would be German) in addition to the Kresy (eastern Poland) in 1939? In such a scenario, the Soviet Union will expand...