AHC and WI: Stalin makes Finland communist?

Well, the terrain certainly wasn't inviting: 80% of forest and marsh, 10% of labyrinthine lake areas with very dedicated and capable defenders even after the field army would have been defeated. In Lithuania the organized resistance continued till the 50's - I could easily see coherent guerilla operations in Finland till the early the 60's at least. Why should Stalin try for maximum when he could get the minimum by negotiations?
 
Anyway, if we take Estonia as the model, I think Finland would have fared even worse: better escape routes to Sweden, more rooted Nordic society (thus even more resistance), no formal surrender, so the army fighting till the bitter end and supplying the guerilla movement with plenty of arms and the terrain quite suitable for prolonged resistance.

Taking all of this into account I would say that in 1991 the country would have about 50% of descendants of the 1939 population and 50% of the newcomers (ca 3 million of each) with the Soviet population concentrating in Helsinki and the industrial areas along the costs and in some places inland. (Helsinki would be about 60-70% Russian speaking).
 
Finland backed out of the war in 1944 and Stalin accepted, even though the Red Army was really on a roll that year and could have waltzed right into Helsinki if Stalin had wanted it to. So what if Stalin decided to dedicate a couple hundred thousand men to the conquest of Finland and create the "People's Republic of Finland"? What would be the rammifications? I wonder why he didn't.

Like others have pointed out, the Finns fought the Red Army almost to a standstill in the summer-fall of 1944, even when such an amount of troops (nearly 500,000 men) had been committed to the Finnish front that should have been enough to crush the Finnish lines. When the race to Berlin was in a crucial moment and Bagration was ongoing, abandoning the goal of taking Finland and instead opting for a ceasefire with the Finns seemed like a better option than keeping at least a half a million troops fighting against the Finns when they were better used elsewhere.

At that point, the Red Army could have steamrolled the weakened Finnish Army had Stalin wanted to. But a cost-benefit calculation told him it was not worth it. Besides, by making a ceasefire with the Finns the Soviets could make the Finnish Army to expel the German troops in Lapland in 1944-45 and the Red Army could just follow the Finns into Norway after that with significantly less resources used than if the Red Army in 1944-45 would have had to fight both the Finns and the Germans to take the northern part of Finland.

About the future of an occupied Finland post-1945, I agree with Karelian: it would have most likely been a People's Republic rather than getting annexed by the USSR as an SSR. The Finnish SSR would have been a result of a lost Winter War (or Finland caving in to Soviet demands in 1939), but in 1944 that train had most likely passed.

Those better versed with the end of the war in Central Europe can probably estimate what the absense of those circa 300,000-500,000 Red Army troops (that would have to subjugate Finland in late 1944-early 1945) from the fighting in Eastern - Central Europe would have meant for where the Red Army ends up by the end of the war. The Soviets might not reach Austria, say, which might mean a *NATO Austria after the war.
 
Finland backed out of the war in 1944 and Stalin accepted, even though the Red Army was really on a roll that year and could have waltzed right into Helsinki if Stalin had wanted it to. So what if Stalin decided to dedicate a couple hundred thousand men to the conquest of Finland and create the "People's Republic of Finland"? What would be the rammifications? I wonder why he didn't.

Another question would be what the fate of von Mannerheim could be...
 
Another question would be what the fate of von Mannerheim could be...

There's no "von" in the name. The Mannerheim family is Swedish aristocracy, not German.

As for C.G. Mannerheim himself, he will die soon. Whether or not he leaves Finland, whether or not he will be tried as a war criminal by a Communist Finnish tribunal or a Soviet court. He was 77 in 1945, suffered from a serious ulcer for which he was operated several times and IOTL died in Switzerland in 1951. ITTL, what with the shock of Finland losing and being occupied, I'd predict Mannerheim dies essentially of poor health and old age somewhere between 1945-50. I can't see even Stalin going as far as executing a sick, broken old man. No, scratch that, I can see Stalin executing him, though it would serve no real purpose.

That is to say that his fate will not be that interesting really.
 
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Its sort of like how they train elephants. When they are young they're leashes are rope.

When the elephant grows up its leashes are still rope because it doesn't know it can break them at any time. So it remains on the leash.

The Soviet Army post purges in 1939 is the baby elephant. Finland hurt a lot.

So that combined with having to get to Berlin and the ire/bad press they would get from the Western Allies if they did take over the country made it not in Stalin's mind worth the effort.
 
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