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Originally Posted by johndallman
Well, he has a significant problem in understanding how the society he's inside works, and what its weak points are. The Nazis' most fundamental problem is they took on too many opponents at once, and lost the battle of GNP. Your outsider's actual best tactic is to become a special envoy for Hitler and spend his time mentally influencing the leaders of states with which Germany isn't yet at war.
So the UK and France don't go to war over Poland, and maybe even ally with Germany against the Soviets, as Hitler hoped. That should deal with the USSR. You then keep Hitler from declaring war on the USA when the Japanese attack (This is easier because the U-boats haven't been sinking merchant ships in the Atlantic).
However, I suspect this isn't the kind of answer you're looking for.
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A lot of the scenarios that have the Nazis winning have the fundamental fallacy that Hitler was rational. When put like that, people would say, "You think?" But I mean he wasn't even rational in the way Stalin was. He had the mindset of a serial killer not of a Mafia don. He really could NOT avoid getting into a war with the whole world because getting into wars with people gave him thrills. You could say that Churchill liked getting into wars with people too. But he had a reasonable sense of proportion if only from being a self-satisfied member of the ruling class of a comfortable parliamentary state. It is hard to imagine Hitler keeping enough of a lid on himself to avoid going to war with everyone.
Furthermore, militarism was an inherent part of the Nazi platform. It appealed to the desire to reverse WWI, in the sense that a new coach rouses a team that had a bad year. If somehow the rest of the world could have contrived not to get into a war with Hitler, he would have been sorely disappointed.