Man, that's just beautiful - I love reading his notebooks. Just skimming them yields unexpected little gems like "the value of money is roughly logarithmic", which I had never heard before and gets me thinking about progressive taxation.
The final step of the St. Petersburg paradox, which he took far further than I had ever seen before, might be implementing the Kelly Criterion, where the amount you bet is related to the size of your own personal bankroll, but I don't know offhand how to relate that to a probability distribution since the Kelly Criterion is normally calculated with one odds value and one payoff value. At the least, I'd like to see a calculation of how many times you'd have to place the bet before you could be reasonably sure of a positive payout - you could do that easily enough with a monte carlo simulation I guess.