"Rationality" in mathematics has a specific meaning that is slightly different from the daily use of the word. Choosing $2 is called "rational" because "rational" means a deviation from the $2 strategy, provided that the opponent has chosen that and does not change his mind, will result in a net loss of expected payoff, not because of an assumption of competitiveness. Also, being "rational" does not mean getting the best possible payoff, or the best chance at a good payoff. It simply means if the two players happen to be already stuck at the $2 strategy, it's the best choice for them to stay at that strategy.
Congratulations, you can misdefine things! What you have defined above firstly is actually the definition of a Nash Equilibrium, not "rational". I also know there can be multiple Nash equilibria, etc...
I don't believe that rationality has ever been defined in game theory as "minimizing risk of loss," that would be an example of simply making a wrong assumption. If the point of a scenario is to minimize loss then such an action may be rational just as if the point is to maximize gain - neither is default.
With this rule in mind, if both player start reasoning with the assumption that both will pick $100, they will get to the equilibrium point of $2 again.
Right, except you have no proof of that. The only argument seems to be "you assume the other player will play $2, therefore it is best for you to do so." (which if they do, is true, I'm not denying that, that's why it is the Nash equilibrium) This is not the case - the problem in all its history has specifically said that the other person, like you, wants to get as much as he/she can, so I don't see why it's rational to assume them choosing $2 in the first place.
Your assumption of versus random is very different from the assumption used in game theory, that is, your opponent will try to minimise any loss to his payoff. Different assumptions give different results. Also note that minimising loss is subtly different from maximising payoff, which is one of the reasons simple TD does not model human behaviour well.
I have never read anything on game theory that said minimizing risk of loss is the only goal, at any rate, if this is so, it only means those theories on game theory are in fact irrational.
Also, Gooblah
Understandable mistake, I'd recommend reconsidering more of what others have posted, not just myself, as this is a poor argument - even if you try to "add it up" that way, 1/97 * 99 + 1/97*101 + 1/97*x + ... will add up to a lot more than $2-4.