My second prototype was much better than the first. I made the board much simpler, and added more spaces from which players had to pick a card. It's the cards that cause the interesting stuff to happen along the way and without them constantly entering the action, it wasn't very interesting. I tried playing it by myself and actually thought it was fun.
Over the weekend, I snagged the family into playing it. We had some laughs (the whole point of a family board game as far as I'm concerned) and found some more flaws, but on the whole, it was much closer. I'm now working on my third prototype with a cleaner board layout and next, I have to work on the rules and making sure that the money works out reasonably. After another round by myself and the family, I'll try it out with some of my creative writing cohorts at TC3.