I think that the biggest "what ifs?" are:
1. What if Hitler had waited until 1945 to start his conquest when the German Navy alleged that it would have been ready?
2. What if Doenitz had been given the resources he had required at the very beginning of the war?
3. What if Goering hadn't been such a prat and had shared his air power with the U-boats (this would be hand in hand with #2)?
4. (here's a really fun one) What if Churchill had not returned to take command?
Realistically the war, as far as the U-Boats were concerned, needed to be won in the first 2 years or never at all. Their only hope after their early failures was the types XXI and XXIII boats and they came too late.
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