I doubt the strategy of going after warships in order to strip merchants of escorts would have worked even with much more U-Boats available. After all, it doesn't cost that much to churn out something like Flower class or ASW Trawlers - just take cheap civilian ship design, mount a gun, DC rack and ASDIC dome and you've got a vessel capable of taking on a U-Boat while being much less expensive. I suspect Allies could produce cheap ASW ships faster than Germans could destroy them, even if they go after warships alone.
Also, for taking out the lonely escort to finish off entire convoy with deck dun - AI is not flexible enough to scramble every plane from nearby airfields, every warship from nearby port and half the escort of other convoys to rescue ships in danger, to disperse a convoy if necessary or to make good attempt at ramming the "clever" U-Boat to death. Or, to start giving out machine guns to every merchant crew before leaving the port. That's why we can try it and real U-Boats couldn't.
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