Having played Cashflow 101 many many times and won it using every single profession in the game, I do have one criticism.
And that is, that it's too easy to make money on shares in the game. If a company comes up with $1 shares, guess what, I already know that at some point in the game a card with the shares worth $30 or $40 will come up, I borrow to the hilt to buy masses of shares, then sit back and wait.
This gives people a ridiculous concept of the sharemarket. In reality, nobody knows which $1 shares will go to $30, and which will disappear. I've done a lot with shares, believe me, I know what I'm talking about!! And options just magnify the risks (and yes, magnify the returns if you're successful - IF!!!).
101 is great, but in the end it is just a game, with all the limitations that brings with it.