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Editorialists at the Boston Globe are skeptical of the plan — for rather vague reasons of "fairness" — but here’s a neat way [2] that private, innovative entrepreneurship might cause scarce parking spaces in Boston to be used more efficiently.
Although the details differ enormously, this idea reminds me of Fred McChesney’s article [3] on parking spaces in snow-bound Chicago. In both cases, as a valuable commodity (parking spaces) becomes more scarce, private efforts and coordination develop ways of creating private property rights in goods that otherwise would remain free-access goods.