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The new Sony Walkman costs more than you think, here's why
(www.slashgear.com)
This is a most excellent place for technology news and articles.
It also won't matter once you take a step outside; slightest ambient noise is enough to kill most of the advantages a high-end source provides.
That depends: proper Shure IEMs usually do a good job covering ambient noise. Somewhere north of 200 USD you usually get proper in ear monitors… but only if it's from one of the regular professional equipment brands, otherwise you'll probably pay for design or the name and little else.