Choosing a plat/Yachtmaster over a bluesy. Buying said yachtie new then tiring and trading said yachtie for bluesy 9 months later. Very expensive mistake....not quite as expensive as the quartz Cartier tank debacle and Longines Hour Angle I had to have but darn near it. Rarely will you have solid wins with watches but playing with Rolex keeps you losing as little as possible for the sake of the hobby.
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