Say, since everyone is saying that the worst thing Finland could do would be fully committing forces to Leningrad... Why? I don't get it. Would helping the Germans out with the siege really weaken them that much in other areas?
The attack would have been very costly to the Finnish military and the whole nation, which in the following years was in terms of supply dependent on Germany anyway. More death and loss of materiel than IOTL all around, in conditions where the Finnish supply situation was precarious as it was. And even if Finland would have managed to take Leningrad, it would have shared a direct responsibility of the civilians in the city, something the Finnish leadership wanted very much to avoid - history would have seen Helsinki as directly responsible when the Nazis would have killed millions one way or the other and Finland could not have done anything about it, even if it would have wanted to. We need to remember the scale of things here: the city of Leningrad had about as many living souls in it as the entire Finnish nation did.
Like wiking says, there was always the possibility that the USSR would rebound even with Leningrad lost, and if that happened, Stalin (or whoever was in charge then) would have aimed to murder Finland with extreme prejudice. The country would have definitely been joined to the USSR after the war, we likely would have seen hundreds of thousands more Finns dead due to the Soviet retribution, and today Finland, if it existed as a relevant entity, would have a large Russian minority if not an outright majority.
And then there is the "victory" option... With hindsight, we know that even if a Finnish assault on Leningrad would have led to the Nazis winning the war, the general outcome would have been worse than IOTL for everyone involved, Finland included. The positives of any irredentist wet dreams about a Greater Finland necessarily pale in comparison.
Quite simply, with hindsight, the best outcome of WWII for Finland was retaining independence and as much of the prewar territory as possible, while avoiding death and destruction, and that the Allies in the end win the war. The OTL is pretty close to the optimal realistic outcome of the war for the Finnish nation, the loss of the 1920 borders notwithstanding. In the entire war, Finland lost roughly 100 000 soldiers and 2000 civilians. Those civilian losses are mind-bogglingly low for a nation stuck between Stalin and Hitler. The closest comparison among combatant nations in WWII is, I believe, Australia. Also in terms of economic losses Finland still comes ahead in comparison to most other minor Nazi allies, even if we factor in the heavy war reparations to the USSR. For this thread in general, we can say that the outcome of WWII for Finland means that the Finnish leaders did not really do any major strategic blunders. Things could have easily been much, much worse.
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