$2 W/P format is a game of picking winners, not making money. In a contest of 10 races is pretty much over half way through. Its just a up and down position battle for the top 5 at that point.

They should have a $500 imaginary bankroll and you can play it as you please on any race as you please (specific race format is even more stupid). The whole idea of winning at the races is to make money not stacking 3/5 winners and say you are the best.