You are misjudging Donitz's request.
He wanted 300+ submarines at the start of hostilities so he could scour the sea lanes on day 1. The technological disparity aside, Donitz knew that the longer Britain had open sea lanes, the stronger she got. Even without the technological disparity, if the Germans had 300 submarines on patrol by 1943, then the golden window for screwing the British economically has somewhat passed. It takes time to destroy merchant shipping; if you take too long, the enemy can put enough escorts into the water to become insurmountable because they can afford to do so since you didn't wipe out their merchant marine in the first 18 months.
While submarines would not have won the war for Germany historically (she was more or less screwed the moment she invaded Poland), having 300 submarines in place in 1939 to start convoy raiding would have forced the British to devote far more resources to things like destroyers and frigates throughout 1936-1939 (there is no way Germany could build 300 submarines without the British knowing), weakening her position versus Italy and Japan. And while the British were working out the doctrines and technology for defeating WWII era submarines, the Germans would have 300 submarines out killing convoys, not a small trickle of them.