Blood and Gold Caribbean Pre-Installed Game
You could start out as a mercenary, accept an assassination mission, collect your reward, walk into a tavern and spend it all in a game of blackjack. Pick up a hooker, lend “protection” services to her procurer, and get hit with a stool in your face during a street fight. Get enslaved and sent to work in a mine, escape with your fellow prisoners, beat all the guards, then rob convoys with an army of former slaves. Save some gold, buy your first plantation, and get rich by trading sugar. Marry a governor’s daughter, acquire a colony to rule, and declare war against Spain. Spend all your savings on cannons, lose 10 boats, and a corvette during a sea siege. Rush in first during a breach of the fortress in Havana and die from your own flagship’s friendly fire.