While it seems like an interesting point - a kind of 'doubling down' - its not clear cut at all.

Firstly, the dichotomy you presented for the individual is: succeed, live, and make loads of money vs fail, die, and lose a fair chunk. The argument you make with this dichotomy is that the gambling doesn't affect anything. However the reality is that there are many ways for the mission to end - fail, live, lose a fair chunk being notable because when the mission is going sideways the individual becomes incentivised to put themselves and others at greater risk to make a successful outcome more likely. Succeed, live, lose your squad mates, make loads of money becomes more likely as well as fail, live, lose your squad mates.

Secondly, insider trading is and always will be a signal for others. If you're only allowed to bet in one direction it becomes a form of information leak - monitor who is liquidating their assets to gamble on outcomes. For any project it becomes a signal to others - if your boss isn't remortgaging to gamble more then you know its time to jump ship. This will in turn have significant effects on outcomes.