Question: When the ship where Dorie Miller is serving gets torpedoed and the captain is about to die, Dorie tells him "You trained us well". This line has always confused me. Does he mean the captain has trained each of the crew members?
Answer: More of a "you have been a great role model and taught/showed us the proper way to act". He was reassuring the Captain.
Question: The IMDb lists a cameo by Matt Damon during the attack sequence. Can someone point out exactly where he appears?
Answer: He is in the scene where the smaller air-base is being attacked by the japanese. You have to look really closely but he is the driver of one of the jeeps right before the japanese bomb drops (the one that seems to be a dud and then explodes). Also, Matt seems to be one of the gunners on one of the first ships at Pearl Harbor to return fire (this is not verified but in slo-mo, one of the gunners seems to be him).
Question: Why does Evelyn get a Purple Heart? As far as I understand, the only way to get it, is if you are wounded in combat.
Answer: From Dec 7, 1941 to Sept 22, 1943, the Purple Heart was also awarded for meritorious performance of duty. For wounds, "in combat" is much more restrictive than the actual requirements. Any injury caused directly or indirectly by a hostile foreign agency counts, including friendly fire if it was intended to hit an enemy.
Question: Where exactly was Dolittle when pearl harbor was being bombed?
Answer: Probably in Washington. He rejoined active duty in 1940, was assigned to consult with industry re aircraft manufacture; also a trip to England on special mission to evaluate other countries' air power. He requested a return to flying status but was refused. He then was asked to assess feasablity of a air attack on Japan from carrier based planes, and when he asked to lead the mission his request was accepted.