I think the part about the misalignment between the individual and the collective is basically wrong. In the given game, the collective loses money just as the individual does. The collective wealth is the summation of the individuals' wealths, and both the collective and individual wealths drop over time. Write a simulation and try it if you don't believe me. I did, because I couldn't work out how the collective wea…
No, your expected value is indeed positive over repeated iterations: (1.05^i)*w, where i is the number of iterations and w is the starting wealth. The intuition for why this happens is that the losses of the majority are made up by the big gains of a minority. You can even see that after two iterations: Case 1: two heads -- 225% wealth Case 2: heads, tails -- 90% wealth Case 3: tails, heads -- 90% wealth Case 4: two…
(The question can be reformulated such that this could be the case.)