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Accurately assessing the probability of winning is the most challenging aspect of applying the Kelly Criterion. Overestimating one’s edge can lead to excessive betting and increased risk. Therefore, thorough research and objective analysis are essential. While the Kelly Criterion isn't a foolproof system, it provides a valuable framework for optimizing bet sizing and maximizing long-term profitability. It’s a sophisticated tool best suited for experienced players with a strong understanding of probability and risk management.