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Why/When to upgrade from stock buds?
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Long car rides as a kid led me to my first couple of headphone purchases (cheap sony "monitor" headphones <$40). As far as portable audiophile tendencies that was a direct result of travel for work and already being pretty in to my home stereo for many years. UE Triple-fi 10's on super-sale paired with a Cowon J3/my phone got me hooked on portable hifi.