>This introduces an extraordinarily massive risk factor - to real assets - to the equation, that you're not accounting for.

No it doesn't. It's identical, except that rolling your bets gives you the additional option which can only be considered more valuable.

And interestingly in this case, Buffet will actually provide the same opportunity if it comes to it. If you get the first couple rounds of the bracket correct, Buffet will be right there with a check offering to buy you out of your position.