hey, thanks for the blog post and your reply! I think I follow - a generalization of a coin-flip type game. I agree that if you have more starting money, you would never lose. From the binary search idea, even if chosen adversarially, the worst case is still log2(100) ~= 6.6. So if you get 1,000 guesses or just any number of guesses >= 7 you literally can't lose. Then you should definitely play.
Setting the limit at 5 brings you to the interesting point of there being a good mix of win/loss outcomes. 4 would be too few guesses and you'd very likely lose, and 7+ you'd definitely win. So the question is only interesting _because_ the limit is chosen so that the spread puts your odds on both sides of the 0 line. Otherwise it'd be clear cut.
The standard deviation being ~$1 is interesting. To me that suggests that with a mean of $0.07 and a deviation of +/- $1, it's essentially 50/50 odds. There's technically a slight edge in your favor, probably 53/47, but barely. So given a game with essentially no edge, would you play? Framing it that way - deciding to what degree the game is winnable - it's essentially not. You should not particularly expect to win, no matter your strategy.
I think part of the trick with the Ballmer question as well is the question is not necessarily about 'can you find an optimal strategy?' - it's 'do you play the game or not?'. The paths chosen within the round don't ultimately matter to that question. It's only intermediately necessary to model the intra-round decision paths in order to get to the overall win/loss distribution for a single round.
If you do end up getting the time, do make another blog post!