Well, there we go - another case of 'everybody knows' being wrong. Perhaps 'a stupid twaddling fellow' is the reason for Star Trek naming Harry Mudd, or maybe they just liked the sound.
I'm always skeptical of reports of cross-dressing since that is a favorite slur of certain types of people against those whom they dislike or disrespect. From what I've heard, the Hoover report was based on a single 'witness' and given credence by his life-long live-in 'friend'. For myself, I think Goering was far too fond of uniforms to try a dress... but many a man has been, um, 'adventurous' once or twice in his life, so when the alcohol starts flowing, who knows? There's many a report of soldiers and sailors in drag, mostly just in good fun. My opinion is that it is like reports of Napoleon being short or Hitler uni-testicular: a not-proven slur that is just nasty enough to be enjoyable.
Anyway, we are a long way off the elektroboot.
In WW2, sonar (or asdic) was a newly-developed technology. Ships could not profitably use it above a crawling speed and aircraft (to my knowledge) did not have anything like the sonobuoys developed later. So it seems reasonable to me that a U-boat capable of remaining submerged for much longer times, and able to manage a high underwater speed for short periods, would have had a better survival rate than a type VII. It represents an improvement, not a shield against detection, but it would have been an advantage.
Experiments post-war (with USS Albacore among others) showed it was possible to achieve very high speeds underwater by adopting a delphinoid or teardrop hullform. Post-war developments in ASW also pointed out that it was not speed but noise that could get a sub targeted and sunk. This is why nuclear subs worry about noise from reactor pumps, why propeller design was so important that supercomputers were needed to solve their math, and why very fast subs like the Akula were eventually abandoned as a dead end. In modern anti-submarine warfare, if you can hear it you can kill it - and modern ASW has Dumbo-sized ears with detectors on ships, planes and on the ocean floor.
So I think that noise was undesirable in WW2-era submarines, but - since the goal was not so much to kill subs as to drive them off and away - a high escape speed might help a sub slip away from an escort that had to return to its convoy. Once the Allies got air-cover in the mid-Atlantic, the U-boat war was - barring some great forward leap - decided, though not over. The Elecktroboot might have prolonged German successes, but given Allied superiority in escorts, aircraft and the ability to build merchant ships, I can't see that it was going to turn the tide. That's a highly if-maybe answer, but that's the best I've got.
Now again, this is just my opinion, but I think that IF Germany was going to 'win' a U-boat war, we need to define 'win'. A complete victory - isolating Britain by reducing her imports to the point that the British government must seek peace - seems to me to have been unachievable. You'd need a substantially larger pre-war German U-boat fleet, an Admiralty unwilling to build escorts or convoy, and perhaps some other pro-German events in order for that to happen and I think the chances of all that being true are slim-to-none.
But a narrower definition - winning by an attrition strategy, costing the Allies more men and materiel than Germany was losing - might have been achievable. You'd still need a better-prepared U-boat fleet (and one that didn't alarm the British into building more escorts to counter it), less intelligent defensive preparations and so on. In this case, developing the next generation of U-boat early and switching production intelligently would have reaped benefits. Forcing the Allies to build even more shipping and materiel, and to lose more ships and cargo, could pay off... but first, I think there are too many things Germany would have to do right and Britain do wrong for even this narrower success to be achieved. The best you could do would be to inflict the same kind of pain as the bomber campaign.
Now, if you add up the costs of the Allied bomber campaigns, add in the cost of German fighter and AA defenses, add in (somehow) the German lives and productivity lost, then balance that against the cost of the U-boat campaign for the Allies in sailors, aircraft, merchant ships and escorts. minus the cost of producing and crewing the U-boats... well, then I don't know. I lost myself somewhere in all those qualifiers. But the stark fact is that Britain went to a bomber campaign because she had no other effective way to hit Germany, and Germany conducted a U-boat campaign because, lacking heavy bombers, it was an effective way to hit Britain. Some people on each side might have thought bombers or subs would be a war-winning weapon but most, I think, just wanted to hurt the enemy.
Given the production advantage of the US-UK-USSR alliance, a German U-boat campaign would have had to be much more effective than a bomber campaign to yield the same percentage of production invested versus destroyed, in order to be labeled a victory. I'm not aware of anyone having done that cost/benefit survey for the two campaigns, but if anyone has - please let me know. I suspect it would not favor Germany and I am unable to come up with a strategy that benefits her more.
Just my opinion here - but IF Germany was going to extend the high tonnage losses inflicted on the Allies early in the war, they would have needed something that could minimize detection by air and strike accurately from some distance. The Elektroboot was probably the best they could do toward the former, although they needed them in large numbers and early on - say in 1942-43 - so that even-more-improved models would be entering service in 1944-45. (The thought of trying to deploy a fleet of Walther turbine U-boats is terrifying - for their crews.) And Germany would have needed a reliable homing torpedo developed and deployed in numbers at the same time. Thirdly, Germany needed really good intelligence on where convoys were, accurate and early enough to be able to concentrate a wolfpack - and they needed the Allies to NOT be able to figure out where the U-boats were gathering.
So that's my take: Germany could not gather the strategic and operational intelligence they needed OR keep the Allies from having the intelligence that they needed. For me, that's the real critical point, and the Elektroboot did not address it. Additional tactical strength was not going to redress a loss of strategic and operational intelligence.