When I was around junior-high age, my mom assigned me a project to create a board game about the history of Australia, which we were studying at the time. It became the only school project that ever made me cry - and not because I had a hard time making it. No... it was because it was just too realistic. You started out as a criminal from England, drawing a card randomly to find out what you did (stealing bread? insulting the Queen?), and you land in Australia as an indentured servant. You got stuck in a loop of manual labour trying to earn your way out of servanthood and hoping that you and your family wouldn't die of any number of things. Once you earned that, you then had to earn the money for tools and land to start your own place. Then you finally moved onto your farm where it turned into a subsistence farming game of hoping you didn't starve to death. We all played it together and at some point both my sister and I cried out of the sheer frustration of realizing that the game was impossible to win.

The Australia game (now in the safekeeping of my brother to protect it from me ripping into a thousand tiny little pieces) was probably the most memorable project I ever did and I remember SO MUCH about the life of early Australian settlers. So now, we do a lot of what I call board-game schooling. I am building a collection of good educational board games, which cover every subject you can think of. So far we have some really amazing games:

Snail's Pace Race - a noncompetitive game for preschoolers to learn colors and counting
Checkers
Dominoes
Monopoly
Junior Scrabble - even younger kids can get in on this since it starts out with letter matching
The Farming Game - build up a farm and learn money management, how debt works, etc.
Geography puzzles
Sounds of the Seashore - from the makers of Cranium, this is a memory game that also uses recognizing sounds
Lord of the Rings Risk - this is really almost the same as regular Risk except that it's only mission Risk.
Risk - strategy game to take over the world, lol.
Tide of Iron - this is a massive game we got the other day and so far we've set it up and that's as far as we got. It has a pretty big learning curve but you recreate specific, real battles from WW2 and there's a LOT of detail involved in the strategy.
Settlers of Catan - probably my favorite game, you build up villages and collect resources to become the most powerful tribe. I just taught Ana this yesterday and she won. Really. We've tried hard to be non-competitive but I think the competitive spirit is inborn, lol.

My Wish List of Games I've Played Before

Made for Trade - this game sort of recreates the economy of Colonial America - barter and trade and earning shillings.
Apples to Apples - a great creative thinking word game where you have to make up reasons that one word is associated with the other. Requires some convincing stage presence, lol.
Pick Two - crossword racing game where you have to build words with random letters faster than everyone else
By Jove - this doesn't seem to be out anymore, or at least on Amazon, but is a great game about classical myths. You start out as a mortal and go to war for Helen of Troy, speak to the Oracle, or hire Hercules for a quest.
Pyramids and Mummies - decipher rebus writing to build a pyramid or try to race to the mummy chamber
Set - ok, not technically a board game, but Set is a Mensa-designed card game that seems deceptively simple. You have to match cards that are either all the same, or all different. It's really very challenging.
Balderdash - bluff your way to winning by making up definitions to obscure real words, and try not to pee your pants laughing
The Amazing Labrynth - fit together maze pieces until you can get specific treasures