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The Empire State Building
The Empire State Building was designed to have a Zeppelin port on the roof. The Great Depression meant that companies weren't starting up and people couldn't afford expensive office rent. It didn't actually become profitable until the 1950s. In 2006, a judge granted an injunction against the City of San Francisco to put in new bicycle lanes. To install those bicycle lanes took the city 2.5 years plus 1353 pages of paperwork; it cost $1 million just to pay the clerks who dealt with regulatory hurdles.