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pengvado comments on Heuristics and Biases in Charity - Less Wrong
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Okay, here's the model: the expected utility of $1 to chosen top 5 charities is nearly equal (due to inaccuracy in evaluation of the utility), and the charities are nearly linear (not super-linear). The expected utility of donating $x to charity i is x*a[i] , and for top 5 a[i] the a[i] values are very close to equal. [They are very close to equal because of your inability to evaluate the utilities of donations to charities]
(for reasonable values of x; we already determined that multi-billionaire needs to diversify)
Thus the combined utility of paying $100 to each of the top 5 charities is then nearly equal to utility of paying $500 to the top one. There is slight loss because the expected utility of the #1 charity is very slightly above that of #5.
At the same time, the strategic reasoning is as follows: the function i (and people like me) used for selecting top (or top 5 even) charities may be exploitable. When the donation is split between top 5, each has 1/5 the incentive to exploit, so the decision to split between top 5, while unable to affect anything about the contribution right now, affects the future payoff of exploitative strategies (and if known beforehand, affects the past payoff estimates as well).
Of course the above reasoning does not work at all if you are grossly over confident in your evaluations of charities and assume some giant differences between expected utility of the top 5, differences which you furthermore had detected correctly.
If there's many charities competing to exploit the same ranking heuristic, then your proposal replaces an incentive of (probability p of stealing all of the donations) with (probability 5*p of stealing 1/5 of the donations). That doesn't look like an improvement to me.
http://lesswrong.com/lw/aid/heuristics_and_biases_in_charity/63gy - second half addresses specifically why "5p * 1/5" might be preferred to 1p. In short, "5p * 1/5" produces a bell curve instead of an "all or nothing" gambit.
The effort towards exploitation of a ranking heuristics is not restricted to set [the most convenient for you value that you pick when you rationalize], 0 . The effort to pay off curve is flattened out at the high effort side when the higher level of efforts don't get you any better than being in the top 5.
It is clear you are rationalizing; the 5p>1 when p>0.2 (which it can be if one is to expend sufficiently greater effort towards raising p than anyone else); and thus 5p can't possibly make sense.