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You might win $100 or $200 and you end up losing $400 to try and do this.... so this is a gamble on a gamble. 
That said, I have won some money in the past with the Eddie challenges, but I almost always end up breaking even or making a small profit.
That said, I have won some money in the past with the Eddie challenges, but I almost always end up breaking even or making a small profit. It wont happen if you have a limit for the challenge. When I want to participate in such contest/challenge, I have to set my limit. I need to predict how much is the possible reward I'll get if I complete the challenge and I will not spend more than the possible reward (max 50%). Lets say the possible reward is $100, I will try it with $50 only but I will also set a limit on one other thing. If I have a luck with my session but I have not reach the challenge, I'll stop to hunt the challenge.