Gotta start with the dinky little S-Class. It's such a hopeless piece of junk that you can't help but love it.
You also appreciate the luxuries of a Gato or a Balao a lot more if you start out in an S-Class. Stern tubes! Bigger torpedoes! Enough fuel for months! Radar! Even the Porpoise feels like an awesome boat after you've spent a few patrols in an S-Class.
My favorite campaign (running RSRDC) is starting in Manila in 1941 in an S-Class boat. There's nothing quite like encountering the Japanese invasion fleets for the Philippines with something like 20 destroyer escorts and having to face them in your pitiful little S-Class.
That campaign also does a great job of showing how bad things went early in the war for the Allies. Up at Pearl, you're sort of isolated from the early disasters once the fires from December 7 stop burning. Down in the East Indies you have to keep changing bases because the Japanese keep taking over your old base. You start in Manila, then get chased to Java, then get chased down to Perth.
On the bright side, Perth also puts you close to the best hunting grounds that I've found so far in the game.
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