That means your $100 in purchasing power gets you five new games: the publishers, developers, and retailers only benefit when you buy new product. We're trying to show them how used games can work in their favor if you cut out the GameStop middleman.
Edit: as for the uncertain price, we're working on it. With our StandingOffers, we might be able to find people willing to guarantee you $30 or $35 up front.
As an example of how that works, right now, I'll pay $25 for a platinum Wavebird (http://www.dawdle.com/product.php/wavebird-wireless-controll...).
I am not saying that Dawdle might not be a better deal for the end consumer. Certainly lower margins means cheaper games means more games sold. But I don't think GameStop are crooks, they simply have an alternative business model. They might be more expensive, but in exchange they offer a different service (guaranteed prices, no hassle with online selling of your game). I don't know GameStop or Dawdle, btw.
As for the original case, it makes no difference who buys the used game, what people seem to care about is the amount of money spent for buying new games. And that is the same for GameStop and for Dawdle.