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SecondWind comments on The Pascal's Wager Fallacy Fallacy - Less Wrong
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I read and understood the Least convenient possible world post. given that, then let me rephrase your scenario slightly
If every winner of a certain lottery receives $X * 300 million, a ticket costs $X, the chances of winning are 1 in 250 million, you can only buy one ticket, and $X represents an amount of money you would be uncomfortable to lose, would you buy that ticket?
answer no. If the ticket price crosses a certain threshold, then I become risk averse. if it were $1 or some other relatively inconsequential amount of money, then I would be rationally compelled to buy the nearly-sure loss ticket.
If you'd be rationally compelled to buy one low-cost ticket, then after you've bought the ticket you should be rationally compelled to buy a ticket. And then rationally compelled to buy a ticket.
Sure, at each step you're approaching the possibility with one fewer dollar, but by your phrasing, the number of dollars you have does not influence your decision to buy a ticket (unless you're broke enough that $1 is not longer a relatively inconsequential amount of money). This method seems to require an injunction against iteration.