docassemble - docassemble is a free, open-source expert system for guided interviews and document assembly.
Port Royale 3 - Port Royale 3 combines the elements of Trading, Strategy, Pirates, and Adventure with Business Simulation by Gaming Minds and published by Kalypso Media Digital.
HotDocs - Template-driven, automated document & form assembly software
The Pirate: Caribbean Hunt - The Pirate: Caribbean Hunt is an Addictive, Adventure, Strategy, Trading, Online, Single and Multiplayer video game released by Home Net Games.
Woodpecker - Legal document automation for solo & small firms. Simple to use, works in Word, connects to everything.
Sid Meier’s Pirates - Sid Meier’s Pirates is an Action-Adventure, Strategy and Single-player video game created and published by MicroProse.