This touches on what for me is one of the big open questions on what it means to act rationally. I question the common position that the kinds of ‘irrational’ decisions you describe are actually all that irrational. Many such decisions seem to be rational decisions for an agent with a high time preference at the moment of decision. They may seem irrational from the perspective of a future self who looks back on the decisions when dealing with the consequences but I see the problem as more one of conflicting interests between present selves and past/future selves than one strictly of rationality. As the recent post discussed, rationality doesn’t provide goals, it only offers a system for achieving goals. Many apparently irrational decisions are I suspect rational responses to short term goals that conflict with longer term goals.
If I decide to eat a chocolate bar now to satisfy a current craving, I am not really acting irrationally. I have a powerful short term drive to eat chocolate and there is nothing irrational in my actions to satisfy that short term goal. Later on I may look at the scales and regret eating the chocolate but that reflects either a conflict between short term and long term goals or a conflict between the goals of my present self and my past self (really just alternative ways of looking at the same problem). It is not a failure of rationality in terms of short term decision making, it is a problem of incentives not aligning across time frames or between present and future selves. In order to find solutions to such dilemmas it seems more useful to look to micro-economics and the design of incentive structures that align incentives across time scales than to ways to improve the rationality of decisions. The steps I take to acquire chocolate are perfectly rational, the problem is with the conflicts in my incentive structure.
Treating money as a linear measure of value breaks down when the amounts get sufficiently large. The marginal utility of $10,000,000 is not simply 10 x the marginal utility of $1,000,000 for one thing (for someone who is not already wealthy). Also, for really large amounts of money such that they represent a significant fraction of the total money supply the linear relationship does not even hold ignoring the marginal utility—owning all the money in the world is not simply 100 x more valuable than owning 1% of all the money in the world.
Then of course there is the problem that nobody would take the bet with you since they would know you can’t possibly pay if they were to win. Unless it’s Goldman Sachs taking the bet and they know the government will print the money and bail you out if they win.