Re: Problem: EV++ and risk tolerance in a multiple decision scenario.
This has been discussed to death. That doesn't mean you will get reasonable answers by asking. According to the Kelly criterion, you should be willing to risk about 96.6% of your bankroll, which means you should keep doubling up until the part of your bankroll not on the table is less than about 1/28 of what you have on the table. While most advantage gamblers view the Kelly criterion (maximize the expected logarithm of your bankroll) as a bit too aggressive, it's a good start.
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