I think at this point a distinction should be made between harbor raids and raiding a major enemy naval base.
On the U.S. side of the argument, they made more than a few harbor raids, but those could be considered easier than the Scapa Flow raid.
On the German side, the Scapa Flow raid was a major accomplishment, but it was planned by Donitz himself and was only done once. Allied harbors were difficult to get into, and very well protected.
On the U.S. side, while the Japanese were moving ships into and out of relatively unprotected areas, this wasn't always so (just like their convoys) - witness the above-described raid by Fluckey.
Bottom line: SH4 raids should on the whole be easier (but only barely).
Bottom line #2: good submarine skippers, like good fighter pilots, were talented, tough, arrogant and took some extreme chances, and sometimes even made them work.
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