Good topic Cammy.
For me personally:
Harpoon - naval ships, aircraft, strategic tactics.
Falcon AT - flight simulation physics
Knights of the Sky - How flying was in World War 1
Wings - same as above
Mavis Beacon Teaches Typing - no reason to explain that one.
Ports of Call - how to run (or not run) a shipping company
All of the above had some educational value, I do miss big manuals too (I loved the Falcon 4 manual about 600 pages).