The game features a set of dice, so anecdotes such as this one are not impossible, it's just that you need to be extremely lucky.
You have a finite number of bets you can make in your life, if you waste them by partying, gambling and being high on drugs then yeah, I can see how it can feel like it's impossible to succeed.
And life is a lot easier than these board games, there isn't one winner in life.
Yes, and they deplete their family's centuries-old hoards of wealth within 2 generations.
Also immigrants usually don't come to literak nothing. While its certainly difficult for them, usually there are cultural or religious groups that help them out or they have family that immigrated before them to help them get on their feet.