I can see the concerns here and there are ways to limit this more, but it would be a lot less fun of a contest. We could certainly lower the bankrolls to $10-20/race instead of $50, etc. It would give everyone less money to work with, less exacta combinations to use, etc. But it wouldn't be much fun at all that way.
I've been in my share of handicapping contests, like the big ones that Daily Racing Form sponsors and you'll find that you've got to take chances at high-priced payoffs to have any shot of winning. When you are up against 200+ people with 15 races on the card, sooner or later someone hits a big long shot and buries the rest. It's the same here - you have to take chances. Anyone grinding it out betting $50/win on the favorite or $1 EX boxes is likely not going to win.
The contest is meant to be just like a horse race - exactly that. Some guys shoot out and take the lead, while others can close strong hitting a big ticket in the finale. No lead is ever safe and likewise no one is ever out of winning this.
Have fun today, guys - I'm really looking forward to all the action!