I found Oregon Trail educational when I was young, but maybe in different ways than the game's authors intended. In the early versions of the game, you had to p

I found Oregon Trail educational when I was young, but maybe in different ways than the game's authors intended. In the early versions of the game, you had to purchase food, clothing, and what not. I recall the prices of these changed as you went to various forts. The obvious way to win the game was to buy a negative amount of clothing when the cost of clothing was high - the game performed no numerical checks when purchasing items. You could survive the journey between two forts with a negative amount of clothing, and when visiting the subsequent fort you could purchase all the goods you would need for the entire journey.