I would get your point Secret Master if we were talking a 4 year war..but the problem is time is against Germany from the very start. So it's unlikely that Germany will even have long enough to inflict the damage they need to. I'm skeptical to the extreme that Britain would fold if the US entered the war.
Well, it wouldn't take four years to sink the British merchant marine if Germany had the u-boats up front.
It took a long time to wear down Japan, but the US didn't commit 300 submarines to a rotational schedule raiding shipping on all or most routes leading to Japan. The distances to Japanese ports and shipping routes were longer, so there were routes that were safer. British shipping routes are much closer to Germany, making it easier to poach shipping of all kinds. (Of course, it also means that as the Atlantic Gap closes, its easier to hunt submarines...)
The First Happy Time in 1940 (before HuffDuff and RADAR were making a huge difference) saw Germany sink 282 merchant ships in a four month period
with far fewer submarines than the 300 Donitz had wanted prior to the war. Can you imagine the damage that could have been done in that same four month period if Germany had twice as many submarines? If they had fixed the dud torpedo problem completely by July of 1940? If there was less progress on naval ENIGMA in 1940? These three items (more subs, better torpedoes, better encryption) are all things you can do in the game to win, and they are also things historical Germany might have also accomplished (Donitz more than once complains that the dud torpedo problem should have been fixed sooner if certain engineers ashore had listened to submarine crews).
I should also point out that even Churchill feared the u-boat. Bombing and Sea Lion didn't keep him up at night, and Ghandi never scared him: "...the only thing that ever frightened me during the war was the U-boat peril." I'm not saying he would give up, but even Winston "We'll fight them on the beaches..." Churchill considered the u-boat a real threat. (Maximum fun is reading Donitz's memoirs and having Donitz quote Churchill's other statement that Germany should have bet everything on the u-boat.)
If Britain is facing an acute crisis in supplies and shipping by July of 1941, she is in a bad situation. If the British Isles themselves are bereft of resources and starving for even basic necessities by December of 1941, and she does not have the merchant marine to supply her overseas bases, then even US entry into the war isn't a magic bullet. The US will spend years Lend-Leasing crap to the British and spamming twice as many Liberty ships just to keep Britain afloat, instead of shipping over bombers and the assets for Overlord. This gives Germany more breathing room than she had historically.
If the US isn't in the war and Britain is starving for food and resources, there is also the possibility that Commons throws in the towel.
Note: I still don't think Germany can win the war, but we're talking about beating the British, not winning the war in this thread.