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Benquo comments on Personal Benefits from Rationality - Less Wrong
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Upvoted for distinguishing the anecdotal outcome (a loss) from the expected outcome (positive). In other words, anecdotes are only good data when everyone reports on their outcome.
BTW, as long as I could give to a charity I considered worthwhile, this would almost always be a slam dunk regardless of the expected gain from the raffle itself. For example, if I valued the good produced by giving $1 to the charity at $0.95, then $0.05 in expected winnings would be my break-even point, not $1.00
Why would you? Charities differ in effectiveness by far more than 5%..
I meant to imply by "a charity I considered worthwhile" that you're near the utility break-even point already. Obviously if you think the charity only does a tiny amount of good, then you need a bigger expected win to make the raffle it worth playing.