Amusing distractions aside, I'm not sure I explained it properly - you're all (presumably) a bright bunch.
In any case. Game theory suggests the answer is $2 - assuming you start with $100, as the other traveller is entirely rational, he will be looking to maximise his own return and select $99. Knowing that will be his strategy, you underbid him with $98, and he changes with $97, all the way until $2.
This is a fairly useful analogy to a bunch of conflicts, including, most obviously, nuclear deterrence.
The 'real' answer is clearly some mix of $99 and $100. This leaves you with a range of payouts between $99 and $101. The key here is that bidding $2 does not maximize returns, but, rather, minimizes them, through the logic simply of trying to beat the other guy. What the ratios would be is a question for smarter men than me, but it could be as simple as half and half. But game theorists actually
insist that the only, correct answer, is $2. Which is pretty stupid
imo.