You forgot to mention how strange it is to get sent to jail for the crime of landing on a space. Or how unfair it it that you don't even get to pass go!
Anyway, it's all a metaphor, so I don't really see anything wrong with Monopoly logic. Landing on a space to get sent to jail just means you've had the bad luck to either be caught in illegal business dealings or you've been framed. Rolling double to get out of jail means you've had the good luck of a sympathetic court hearing or some new evidence that exculpates you or some shady lawyer mischief that gets you out. And of course, real life business tycoons have plenty of real life get out of jail free cards.