thaskalos,
Not sure if I am qualified to answer your question, but I wouldn't expect any transition to be smooth--like handicapping it will require a lot of hard work, and a never ending quest to improve your methods. However, a lot of what you learned as a handicapper will also apply to the financial markets. I'd recommend reading the book "Fooled By Randomness" by Nassim Taleb. The following is my favorite quote from the book, which can apply to handicapping or any other endeavor...
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"If the science of statistics can benefit me in anything, I will use it. If it poses a threat, then I will not. I want to take the best of what the past can give me without its dangers. Accordingly, I will use statistics and inductive methods to make aggressive bets, but I will not use them to manage risks and exposure."
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That quote alone pretty much sums things up. I am a numbers guy, but I have to constantly remind myself not to let randomness fool me. In the book, Taleb also paraphrases Yogi Berra, i.e.
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"past data has a lot of good data in it, but it is the bad side that is bad."
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For several years running, inverse volatility strategies were some of the most profitable and least volatile trading methods--until one day last year when the trade blew up and many people lost their entire accounts in a matter of hours. The take-away is not to search for an unbeatable strategy, because there isn't any. But, you can use statistical methods to find your bets, just not to manage your risks.
If you are a programmer, the transition might be easier. If so, make MATLAB, R, and Visual Studio your new best friends. But you don't need to be a programmer, since there are many other good programs out there to help you trade.
My advice is to start slowly, don't be fooled, and always manage your risk--i.e. don't blow-up your account. Ultimately you are the one making the decision and taking the risks, so find a method that suits your temperament and your risk tolerance.
Good luck... Que.
