I think @JDOW provided a pretty good summary of our game. (thanks!) I had some random thoughts below.
One point worth noting is that while the axis had better odds in the first Bryansk battle, it was less risky for the Soviets than it appeared. For one, the odds were close (38-62). Secondly, a Soviet win was likely game winning. Third, the balance of forces was such that I would lose more high combat value units early (defensive inf vs offensive inf so a good first roll could change the odds dramatically and the Soviets could retreat if not). Fourth, even if I won, the most likely outcome was heavy attrition on both sides. And that probably would have favoured the allies as I wouldn’t be able to take and hold Volgograd and Caucasus given the allied pressure from both Moscow and the ME.
Instead, the first round went great for me. Round 1 I hit 1.33 less than average but two of my hits were from 3 AA roles and you hit 8 under. Round 2 and 3 were closer but both rounds favoured me. So while at the end of it, we were both diminished, the Soviets were far worse off than expected (down about 15 units more than I was and 2 of those were air rather than land).
So going for this was not as much of a gamble as one might think. I do think a mistake here may have been the decision to continue after the first round. And there was a second battle of Bryansk that was a similar situation that I think was also a mistake (at least after the first round) as once the battle started to go south, the Soviets were losing units that were more valuable to Moscow’s defense.
I’ll note here too that given the risk, it may also have been better for me not to create the opportunity. But I felt if I didn’t go for it then, I would not get another chance at getting Volgograd and Caucasus, and so not to do it would be game losing as well.
An alternative to the attack on Bryansk was to use blockers to delay the Germans from getting Volgograd and Caucasus forcing me to move the stack South if I wanted to take and hold them. I had a small Italian can opener available, so the cost of blockers would have been higher, but the Soviets (and the British) had units to spare. I haven’t perhaps thought this through enough, but I thought that was the other option here and one I might have tried for instead in your shoes.
I also didn’t try to take Moscow or India early because I simply couldn’t. There were a few moments where I might have had decent odds, but nothing certain and I felt more confident that I could get the game economically and those would come later. That certainly became the grand strategy. At the end of the game, I was in a position to take Moscow with 100% odds and I think was perhaps a couple of turns away from putting similar pressure on India, but it took quite a while.
Your allied play is quite challenging. Efficient and I always felt lots of pressure from multiple directions (and often that pressure wasn’t immediately obvious so I had to be very careful).
One critique I had though was that a lot of resources in the pacific were caught up in land units defending Honolulu, Sidney, and the Caroline Islands. That does make those more of a challenge to take, but I thought a lot of those units ended up being wasted. I always had the naval superiority to keep the US on the outside of the pacific but there were a couple of moments where it was somewhat close. A couple of more carriers or 5-10 more subs might have made the difference and so I wonder if that would have been a better use of resources.
The dice went back and forth but might have helped me when I needed them more. I suffered a bit in round 1 but Bryansk 1 went great for me and 2 favoured me too, if not as much. The Japanese air attack on the Chinese inf stack in round 2 also went as well as could reasonably be hoped. The game might have gone very differently if the dice had been different in any one of those.