In fact, if you repeatedly simulate the problem (make sure you use bignums) you will find that the mean gain from swapping is not well behaved at all and refuses to converge. The law of large numbers only applies if the expectation is well-defined.
The lesson here is: when in doubt, explicitly write out the probability space over which you are working. Problems like this and the Monty Hall problem are trivially solvable on paper. There is a reason that mathematicians get all hot and bothered about formalism - it gives you a solid base from which to build correct intuitions.
EDIT Let's write this down properly.
i | gain from swapping if I have the smallest | gain from swapping if I have the largest
1 $2 -$2
2 $4 -$4
3 $8 -$8
etc
There are two arguments.The first is that the situation is symmetric so you can't possibly gain. That is:
E(Gain) = (1/4 * $2 + 1/4 * -$2) + (1/8 * $4 + 1/8 * -$4) ...
= $0 + $0 + $0 + $0 ...
= $0
The second argument is that swapping from small to large is a bigger gain than the loss of swapping from large to small. That is: E(Gain) = (1/4 * $2) + (1/4 * -$2 + 1/8 * $4) + (1/8 * -$4 + 1/16 * $8) ...
= $0.5 + $0 + $0 + $0 ...
= $0.5
Adding up an infinite series is tricky :)