At some point I’ll make an effort post about it, although I think instead of listing my criticisms I may just focus on the one that I think did the most long term damage to the project of socialism in the USSR (the purges).
In brief, while I could get into the morality of purging cadres - whether we’re talking expulsion from the party or all the way up to getting killed - who didn’t actually do anything to deserve it, in the end I’m not really interested in passing any sort of moral judgement of Stalin. I’m only concerned about how that affected how that affected the Soviet project.
And IMO, it was damaging long-term. The party lost so much leadership, power, and influence by losing so many members. That loss created a vacuum that was filled by the bureaucracy. And those bureaucrats (particularly bureaucrats involved in the economy and production) led using the tools they had at their disposal, which was (to greatly oversimplify) to just do whatever you had to do to hit a production target. Source your production inputs however you can, just make it work. And that actually works great for the crash industrialization that helped the Soviets win the war!
But the problem is, you can’t run the economy that way forever. Eventually, in a socialist economy, you need more rational planning. But the bureaucracy under Stalin was actually hostile to things like cybernetics. Khrushchev tried to get around the problems this was creating (bad ideas but he was trying and was limited by the fact he was in charge in a time just before computers and linear programming and stuff like that entered the scene) but by that point bureaucracy was actually stronger than the party. The bureaucracy that cut its teeth under Stalin and was empowered by him knew one way to do things, and they weren’t going to listen to what the party thought needed to be done. In a way the ascension of Brezhnev was the bureaucracy reasserting itself over any further reforms. Things weren’t going to change and it’s no surprise that when you hear about the Soviet economy in the 80s, there’s all sorts of industrial shortages and inefficiencies, and I think you can draw a line back to Stalin for a that.
In an alternate reality where the purges are much smaller, you could have a stronger party with more diverse and better ideas leading the charge. I imagine a not dead Bukharin would have successfully pushed for adoption of cybernetics early in the game to manage the economy, and the USSR would be around today.
I wanted to caveat all this with: this is all my opinion. I am still learning and am open to challenges on any of this.

